Method for production of cis-4-fluoro-L-proline derivatives

Details Method for production of cis-4-fluoro-L-proline derivatives Method for production of cis-4-fluoro-L-proline derivatives

2007-10-09

2007-10-09

Powers, Fiona T (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S533000

Reexamination Certificate

active

10568708

ABSTRACT:
The present invention provides a safer method for production of a cis-4-fluoro-L-proline derivative under milder conditions and in good yield to give a product of high purity on an industrial scale at low cost. Namely, the present invention provides a method for producing a cis-4-fluoro-L-proline derivative, which comprises reacting a trans-4-hydroxy-L-proline derivative of the following Formula [I]:(wherein R1represents a protecting group for an α-amino group, and R2represents a protecting group for a carboxyl group) with N,N-diethyl-N-(1,1,2,3,3,3-hexafluoropropyl)amine in the presence of a hydrogen fluoride-scavenger.

REFERENCES:
patent: 6384234 (2002-05-01), Taylor et al.
patent: 2002-275267 (2002-09-01), None
patent: WO-2006/103986 (2006-10-01), None
L. Demange, et al., “Practical Synthesis of Boc and Fmoc Protected 4-Fluoro and 4-Difluoroprolines from Trans-4-Hydroxyproline,” Tetrahedron Letters, 1998, pp. 1169-1172, vol. 39, France.
G. Giardina, et al., “Facile and Efficient Syntheses of Novel (S)- and (R)-3-Fluoropyrrolidines and 3,3-Difluoropyrrolidine,” Synlett, Jan. 1995, pp. 55-57, No. 5, Italy.

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