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

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

2009-11-06

2011-12-27

Anderson, Rebecca (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S537000

Reexamination Certificate

active

08084622

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:
patent: 7153851 (2006-12-01), Asahina et al.
patent: 2005/0182052 (2005-08-01), Asahina et al.
patent: 2006/0281779 (2006-12-01), Asahina et al.
patent: 2005-239617 (2005-09-01), None
patent: 03/078439 (2003-09-01), None
patent: 2005/026147 (2005-03-01), None
International Search Report issued May 29, 2007 in International (PCT) Application No. PCT/JP2007/054501 corresponding to the parent application of the present divisional application.
Morissette et al., “High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids”, Advanced Drug Delivery Reviews, 56, 275-300, 2004.
Sudha R. Vippagunta, “Crystalline Solids”, Advanced Drug Delivery Reviews, 48, 3-26, 2001.

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