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SE8009074L - PROCEDURE FOR THE PREPARATION OF N-SUBSTITUTED PYRROLIDINES - Google Patents

PROCEDURE FOR THE PREPARATION OF N-SUBSTITUTED PYRROLIDINES

Info

Publication number
SE8009074L
SE8009074L SE8009074A SE8009074A SE8009074L SE 8009074 L SE8009074 L SE 8009074L SE 8009074 A SE8009074 A SE 8009074A SE 8009074 A SE8009074 A SE 8009074A SE 8009074 L SE8009074 L SE 8009074L
Authority
SE
Sweden
Prior art keywords
preparation
formula
reduction
procedure
optically active
Prior art date
Application number
SE8009074A
Other languages
Swedish (sv)
Inventor
J-P Kaplan
H Najer
D C L Obitz
Original Assignee
Synthelabo
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR7623910A external-priority patent/FR2360572A1/en
Priority claimed from FR7635476A external-priority patent/FR2372157A1/en
Priority claimed from FR7719391A external-priority patent/FR2395261A2/en
Application filed by Synthelabo filed Critical Synthelabo
Publication of SE8009074L publication Critical patent/SE8009074L/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The optically active pyrrolidines of formula: are obtained from (R)- or (S)-glutamic acid, by formation of an aldimine with an aldehyde R''CHO, reduction of the imino group to an amino group, cyclisation by the action of an acid, esterification of the carboxyl, conversion of the ester to an amide and reduction. The compounds can be used in the synthesis of optically active benzamides, which have a therapeutic activity, of formula: To this end, they are condensed with a 2-methoxy-5-X-benzoic acid or one of its derivatives. None of the reactions affects the absolute configuration of the asymmetric carbon; thus, (S)-glutamic acid leads to an (S)-amine I and to an (S)-benzamide II. The symbols R', R'' and X are defined in Claims 1 and 8.

Claims (1)

PATENTKRAV den erhAllna fOreningen behandlas med ammoniak fdr framstallning avCLAIMS the obtained compound is treated with ammonia before the preparation of 1. Satt att framstalla en pyrrolidin med formeln LN eller H CONH2 Cs) CONH2 ( R ) eller ICO C°N22 b. CS) CO CONH 2 11" ( R ) eller och den erhallillikreningen reilllas till namnda pyrrolidin. (1,K\s_,7 A ' CH2 C11214H2 eller vari R" betecknar C1_4-alkyl eller H.', eller ja N CH2NH2 CH2 A" Cs) ; den erhallna amiden behandlas med R"COOH eller dess klorid eller anhydrid for framstallning av L le800902V- 9 C 0? .1) 2o09 (71)SYNTHELABO, Paris FR (72)Uppf J-P Kaplan, H Najer, 0 C L Obitz, Plessis Robinson, Paris, Orsay (30)Prioritetsuppgifter 76-08-05 FR 76 23910 76-11-25 FR 76 35476 77-06-24 FR 77 19391 (54)Benamning FOrfarande for framstallning av N-substituerade pyrrolidinerSet to produce a pyrrolidine of the formula LN or H CONH2 Cs) CONH2 (R) or ICO C ° N22 b. CS) CO CONH 2 11 "(R) or and the erhalilli purification is reacted to said pyrrolidine. s', 7 A 'CH2 C11214H2 or wherein R "represents C1-4 alkyl or H.', or yes N CH2NH2 CH2 A" Cs); the resulting amide is treated with R "COOH or its chloride or anhydride to produce L le800902V- 9 C 0? .1) 2o09 (71) SYNTHELABO, Paris FR (72) Uppf JP Kaplan, H Najer, 0 CL Obitz, Plessis Robinson, Paris, Orsay (30) Priority information 76-08-05 FR 76 23910 76-11-25 FR 76 35476 77-06-24 FR 77 19391 (54) Designation Process for the preparation of N-substituted pyrrolidines
SE8009074A 1976-08-05 1980-12-22 PROCEDURE FOR THE PREPARATION OF N-SUBSTITUTED PYRROLIDINES SE8009074L (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR7623910A FR2360572A1 (en) 1976-08-05 1976-08-05 Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals
FR7635476A FR2372157A1 (en) 1976-11-25 1976-11-25 Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals
FR7719391A FR2395261A2 (en) 1977-06-24 1977-06-24 Optically active (2)-amino-methyl-(1)-substd. pyrrolidine derivs. - intermediates for benzoylamino-methyl-pyrrolidine pharmaceuticals

Publications (1)

Publication Number Publication Date
SE8009074L true SE8009074L (en) 1980-12-22

Family

ID=27250658

Family Applications (2)

Application Number Title Priority Date Filing Date
SE7708902A SE7708902L (en) 1976-08-05 1977-08-04 STEREOSPECIFIC SYNTHESIS OF N-SUBSTITUTED PYRROLIDINES
SE8009074A SE8009074L (en) 1976-08-05 1980-12-22 PROCEDURE FOR THE PREPARATION OF N-SUBSTITUTED PYRROLIDINES

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SE7708902A SE7708902L (en) 1976-08-05 1977-08-04 STEREOSPECIFIC SYNTHESIS OF N-SUBSTITUTED PYRROLIDINES

Country Status (20)

Country Link
JP (1) JPS5325563A (en)
AT (1) AT364818B (en)
AU (1) AU510454B2 (en)
CA (1) CA1083586A (en)
CH (2) CH624933A5 (en)
DE (1) DE2735036C2 (en)
DK (1) DK350377A (en)
ES (1) ES461342A1 (en)
FI (1) FI772363A7 (en)
GB (1) GB1555890A (en)
GR (1) GR63594B (en)
IE (1) IE45544B1 (en)
IL (1) IL52645A (en)
IT (1) IT1085696B (en)
LU (1) LU77917A1 (en)
NL (1) NL7708571A (en)
NO (2) NO772745L (en)
NZ (1) NZ184832A (en)
PT (1) PT66894B (en)
SE (2) SE7708902L (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1095415B (en) * 1978-02-16 1985-08-10 Ravizza Spa PROCESS FOR THE PRODUCTION OF AN OPTICALLY ACTIVE BENZAMIDE, OPTICALLY ACTIVE BENZAMIDE SO OBTAINED AND COMPOSITIONS
IT1141095B (en) * 1980-11-27 1986-10-01 Ravizza Spa RESOLUTION PROCESS OF THE SULPYRID RACEMA
SE8602339D0 (en) * 1986-05-22 1986-05-22 Astra Laekemedel Ab AND EFFECTIVE STEREOCONSERVATIVE SYNTHESIS OF 1-SUBSTITUTED (S) - AND (R) -2-AMINOMETHYLPYRROLIDINES
DE4425070A1 (en) * 1994-07-15 1996-01-18 Degussa Process for the preparation of optically active l-substituted 2- (aminomethyl) pyrrolidines
US7531673B2 (en) * 2004-02-18 2009-05-12 Dr. Reddy's Laboratories Limited Preparation of amino acid amides
CN104086475B (en) * 2014-07-15 2016-10-05 苏州天马精细化学品股份有限公司 A kind of preparation method of N-benzyloxycarbonyl group-L-prolineamide
CN106045869A (en) * 2016-06-30 2016-10-26 宜兴市前成生物有限公司 Method for preparing DL-glutamic acid
CN117185977A (en) * 2023-09-20 2023-12-08 江苏阿尔法药业股份有限公司 A kind of preparation method of amisulpride intermediate

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1528014A (en) * 1967-04-24 1968-06-07 Ile De France Process for the preparation of optical isomers of ethyl-1, aminomethyl-2-pyrrolidine
CH507938A (en) * 1968-08-01 1971-05-31 Ile De France Process for the preparation of heterocyclic benzamides

Also Published As

Publication number Publication date
DE2735036C2 (en) 1983-10-13
IL52645A0 (en) 1977-10-31
IL52645A (en) 1980-02-29
AT364818B (en) 1981-11-25
DE2735036A1 (en) 1978-02-16
CH626341A5 (en) 1981-11-13
ATA577377A (en) 1981-04-15
AU510454B2 (en) 1980-06-26
CH624933A5 (en) 1981-08-31
NO772745L (en) 1978-02-07
PT66894B (en) 1979-01-26
GR63594B (en) 1979-11-26
IE45544B1 (en) 1982-09-22
NO812871L (en) 1978-02-07
CA1083586A (en) 1980-08-12
IE45544L (en) 1978-02-05
NZ184832A (en) 1979-11-01
IT1085696B (en) 1985-05-28
FI772363A7 (en) 1978-02-06
GB1555890A (en) 1979-11-14
JPS5325563A (en) 1978-03-09
PT66894A (en) 1977-09-01
ES461342A1 (en) 1978-06-01
NL7708571A (en) 1978-02-07
SE7708902L (en) 1978-02-06
LU77917A1 (en) 1977-11-14
DK350377A (en) 1978-02-06
AU2764177A (en) 1979-02-08

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