GB833820A - Improvements in or relating to the preparation of pyrrolidyl esters and quaternary compounds thereof - Google Patents
Improvements in or relating to the preparation of pyrrolidyl esters and quaternary compounds thereofInfo
- Publication number
- GB833820A GB833820A GB32474/57A GB3247457A GB833820A GB 833820 A GB833820 A GB 833820A GB 32474/57 A GB32474/57 A GB 32474/57A GB 3247457 A GB3247457 A GB 3247457A GB 833820 A GB833820 A GB 833820A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxymethylpyrrolidine
- formula
- allyl
- alkyl
- pyrrolidyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 title abstract 5
- -1 pyrrolidyl esters Chemical class 0.000 title abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 3
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229940043131 pyroglutamate Drugs 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 238000011282 treatment Methods 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- BMKZGNGSUYJXAN-UHFFFAOYSA-N (1-acetylpyrrolidin-2-yl)methyl acetate Chemical compound CC(=O)OCC1CCCN1C(C)=O BMKZGNGSUYJXAN-UHFFFAOYSA-N 0.000 abstract 1
- CTMMLLPSNRLJJH-UHFFFAOYSA-N (1-butanoylpyrrolidin-2-yl)methyl butanoate Chemical compound C(CCC)(=O)N1C(CCC1)COC(CCC)=O CTMMLLPSNRLJJH-UHFFFAOYSA-N 0.000 abstract 1
- RCEKCRDWPFVWCG-UHFFFAOYSA-N (1-butylpyrrolidin-2-yl)methanol Chemical compound CCCCN1CCCC1CO RCEKCRDWPFVWCG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- VCOJPHPOVDIRJK-UHFFFAOYSA-N 1-Methylpyrrolidine-2-methanol Chemical compound CN1CCCC1CO VCOJPHPOVDIRJK-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 abstract 1
- QBBAJUQOYIURHA-ZETCQYMHSA-N butyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCOC(=O)[C@@H]1CCC(=O)N1 QBBAJUQOYIURHA-ZETCQYMHSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 abstract 1
- 229940017219 methyl propionate Drugs 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 150000003109 potassium Chemical class 0.000 abstract 1
- HVVNJUAVDAZWCB-UHFFFAOYSA-N prolinol Chemical compound OCC1CCCN1 HVVNJUAVDAZWCB-UHFFFAOYSA-N 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
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
- C07D207/10—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
- C07D207/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Abstract
Compounds of formula <FORM:0833820/IV (b)/1> wherein Ph represents phenyl and R is C1-4 alkyl or allyl, are prepared by reacting a 1-alkyl-2-hydroxymethylpyrrolidine of formula <FORM:0833820/IV (b)/2> with an acid halide of formula <FORM:0833820/IV (b)/3> where X is chlorine or bromine, to give a compound of formula <FORM:0833820/IV (b)/4> which is then converted to the product (I) by treatment with water and a base. The compounds (I) in which R is C2-4 alkyl or allyl and salts thereof are claimed per se. The treatments with water and the base may be simultaneous or successive. The first stage of the reaction may be effected in a solvent, e.g. butanone. The products (I) may be reacted with an ester R1Z to form a quaternary salt of formula <FORM:0833820/IV (b)/5> where R1 is alkyl or aralkyl and Z is a halogen, alkyl sulphate or aryl sulphonate radical. The anion Z may be exchanged for other anions, e.g. by reaction with the silver salt of an appropriate inorganic or organic acid. Optically active products may be resolved into their isomers. Starting materials prepared are 1-methyl-2-hydroxymethylpyrrolidine by the formaldehyde/formic acid methylation of 2-hydroxymethylpyrrolidone obtained by LiAlH4 reduction of butyl pyroglutamate; 1-ethyl-, 1-n-propyl- and 1 - n - butyl - 2 - hydroxymethylpyrrolidine by the LiAlH4 reduction of (1-acetyl-2-pyrrolidyl)-methyl acetate, 1-n-propionyl-2-pyrrolidyl)-methyl propionate and (1-butyryl-2-pyrrolidyl)-methyl butyrate respectively, these being obtained by the action of acetic, propionic or butyric anhydride on 2-hydroxymethylpyrrolidine; 1-isopropyl and 1 - allyl - 2 - hydroxymethylpyrrolidine by the LiAlH4 reduction of butyl 1-isopropyl- and 1-allyl-pyroglutamate respectively, these being obtained by the action of isopropyl iodide or allyl bromide on the potassium derivative of butyl pyroglutamate. The Provisional Specification refers to compounds corresponding to I, III and IV, in which one phenyl group is replaced by cyclohexyl. Specification 820,503 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32474/57A GB833820A (en) | 1957-10-17 | 1957-10-17 | Improvements in or relating to the preparation of pyrrolidyl esters and quaternary compounds thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32474/57A GB833820A (en) | 1957-10-17 | 1957-10-17 | Improvements in or relating to the preparation of pyrrolidyl esters and quaternary compounds thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB833820A true GB833820A (en) | 1960-04-27 |
Family
ID=10339135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32474/57A Expired GB833820A (en) | 1957-10-17 | 1957-10-17 | Improvements in or relating to the preparation of pyrrolidyl esters and quaternary compounds thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB833820A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355458A (en) * | 1964-04-16 | 1967-11-28 | Merck & Co Inc | Nu-alkenyl pyroglutamic acid amides, salts and 1, 1' methylene bis-(allyl pyroglutamates) thereof |
| EP0325984A3 (en) * | 1988-01-25 | 1991-01-02 | Hoechst-Roussel Pharmaceuticals Incorporated | 5-substituted 1-/4-(1-pyrrolidinyl)-2-butynyl/-2-pyrrolidones and related compounds, a process for their preparation and their use as medicaments |
| JP2008525359A (en) * | 2004-12-24 | 2008-07-17 | ノバルティス アクチエンゲゼルシャフト | Quaternary ammonium salts as M3 antagonists |
| JP2008529965A (en) * | 2003-06-24 | 2008-08-07 | ノバルティス アクチエンゲゼルシャフト | Piperidinium and pyrrolidinium derivatives as ligands for muscarinic M3 receptors |
-
1957
- 1957-10-17 GB GB32474/57A patent/GB833820A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355458A (en) * | 1964-04-16 | 1967-11-28 | Merck & Co Inc | Nu-alkenyl pyroglutamic acid amides, salts and 1, 1' methylene bis-(allyl pyroglutamates) thereof |
| EP0325984A3 (en) * | 1988-01-25 | 1991-01-02 | Hoechst-Roussel Pharmaceuticals Incorporated | 5-substituted 1-/4-(1-pyrrolidinyl)-2-butynyl/-2-pyrrolidones and related compounds, a process for their preparation and their use as medicaments |
| JP2008529965A (en) * | 2003-06-24 | 2008-08-07 | ノバルティス アクチエンゲゼルシャフト | Piperidinium and pyrrolidinium derivatives as ligands for muscarinic M3 receptors |
| JP2008525359A (en) * | 2004-12-24 | 2008-07-17 | ノバルティス アクチエンゲゼルシャフト | Quaternary ammonium salts as M3 antagonists |
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