Process for producing 3,4-disubstituted pyrrolidine derivative and production intermediate thereof
US8084622B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Nov 6, 2009 |
| Grant date | Dec 27, 2011 |
| Priority date | — |
| Expiry date | Jul 29, 2030 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D207/16
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
An industrially advantageous process for the production of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof that is useful as an intermediate for the production of novel antimicrobial agents 10-(3-cyclopropylaminomethyl-4-fluoropyrrolidinyl)pyridobenzoxazine carboxylic acid derivatives.Highly stereoselective asymmetric hydrogenation of 1-protected-4-alkoxycarbonyl-3-oxopyrrolidine, followed by ester hydrolysis, followed by amidation with cyclopropylamine gives crude crystals. The crude crystals are purified by recrystallization to give a novel compound (3R,4S)-1-protected-3-cyclopropylcarbamoyl-4-hydroxypyrrolidine or an enantiomer thereof at high optical purity. The use of these intermediates enables industrial production of high-quality products of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof. The process is highly simple and can produce the desired products at high purity and stable yields.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.