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GB1470030A - Optical resolution of 1-t-butylamino-2,3-dihydroxy-propane - Google Patents

Optical resolution of 1-t-butylamino-2,3-dihydroxy-propane

Info

Publication number
GB1470030A
GB1470030A GB5063275A GB5063275A GB1470030A GB 1470030 A GB1470030 A GB 1470030A GB 5063275 A GB5063275 A GB 5063275A GB 5063275 A GB5063275 A GB 5063275A GB 1470030 A GB1470030 A GB 1470030A
Authority
GB
United Kingdom
Prior art keywords
butylamino
dihydroxypropane
diastereoisomer
solution
optical resolution
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB5063275A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1470030A publication Critical patent/GB1470030A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1470030 Optical resolution of 1-t-butylamino- 2,3-dihydroxypropane MERCK & CO Inc 10 Dec 1975 [13 Dec 1974 25 Sept 1975] 50632/75 Heading C2C Mixtures of enantiomers of 1-t-butylamino- 2,3-dihydroxypropane are optically resolved by (1) treating a solution of the mixture with a resolving agent selected from S-pyroglutamic acid, R-pyroglutamic acid, L-tartaric acid and D-tartaric acid (2) separating from the solution the solid diastereoisomer which forms and (3) recovering from the diastereoisomer a single enantiomer of 1-t-butylamino-2,3-dihydroxypropane, e.g. by treating it with a base or running a solution of the diastereoisomer through an ion-exchange resin. The initial mixture of enantiomers of 1-t-butylamino-2,3-dihydroxypropane may be made by reacting t-butylamine with glycidol.
GB5063275A 1974-12-13 1975-12-10 Optical resolution of 1-t-butylamino-2,3-dihydroxy-propane Expired GB1470030A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US53254774A 1974-12-13 1974-12-13
US61594175A 1975-09-25 1975-09-25

Publications (1)

Publication Number Publication Date
GB1470030A true GB1470030A (en) 1977-04-14

Family

ID=27063872

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5063275A Expired GB1470030A (en) 1974-12-13 1975-12-10 Optical resolution of 1-t-butylamino-2,3-dihydroxy-propane

Country Status (10)

Country Link
JP (1) JPS51118711A (en)
AU (1) AU510799B2 (en)
CA (1) CA1064943A (en)
DE (1) DE2556040C2 (en)
DK (1) DK532575A (en)
FR (2) FR2294151A1 (en)
GB (1) GB1470030A (en)
IE (1) IE42206B1 (en)
NL (1) NL7513818A (en)
SE (1) SE435499B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4588694A (en) * 1982-08-13 1986-05-13 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for production of optically active oxazolidinone derivative

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01149775A (en) * 1987-12-07 1989-06-12 Kawaken Fine Chem Co Ltd Method for producing optically active 2-methylpiperazine
US5684159A (en) * 1995-05-30 1997-11-04 Rhone-Poulenc Rorer S.A. L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds
IN187238B (en) * 1995-06-30 2002-03-09 Astra Ab
EP3433230A1 (en) * 2016-03-25 2019-01-30 The U.S.A. As Represented By The Secretary, Department Of Health And Human Services Crystal forms and methods of synthesis of (2r, 6r)-hydroxynorketamine and (2s, 6s)-hydroxynorketamine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2528267A (en) * 1950-10-31 Eobeet j
US3116332A (en) * 1958-10-17 1963-12-31 Du Pont Resolution of racemic aminoisopropanol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4588694A (en) * 1982-08-13 1986-05-13 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for production of optically active oxazolidinone derivative

Also Published As

Publication number Publication date
AU8722075A (en) 1977-06-09
DE2556040A1 (en) 1976-06-16
JPS51118711A (en) 1976-10-18
NL7513818A (en) 1976-06-15
SE435499B (en) 1984-10-01
CA1064943A (en) 1979-10-23
FR2294151A1 (en) 1976-07-09
DK532575A (en) 1976-06-14
FR2303790A1 (en) 1976-10-08
DE2556040C2 (en) 1986-05-07
AU510799B2 (en) 1980-07-17
SE7513307L (en) 1976-06-14
IE42206B1 (en) 1980-06-18
FR2303790B1 (en) 1980-07-18
FR2294151B1 (en) 1979-04-06
IE42206L (en) 1976-06-13

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19951209