Process for producing 3,4-disubstituted pyrrolidine...

Details Process for producing 3,4-disubstituted pyrrolidine... Process for producing 3,4-disubstituted pyrrolidine...

2007-03-08

2010-02-23

Shiao, Rei-Tsang (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07667049

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.

REFERENCES:
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Morissette et al. “High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids.” Advanced Drug Delivery Reviews 2004, 56, 275-300.
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International Search Report issued May 29, 2007 in the International (PCT) Application PCT/JP2007/054501 of which the present application is the U.S. National Stage, abs only.

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