Process for producing optically active 1-alkyl-substituted...

Details Process for producing optically active 1-alkyl-substituted... Process for producing optically active 1-alkyl-substituted...

2004-06-08

2008-07-01

Davis, Brian J (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C564S392000

Reexamination Certificate

active

07393979

ABSTRACT:
The present invention relates to a process for producing an optically active 1-alkyl-substituted 2,2,2-trifluoroethylamine, which is an important intermediate of medicines and agricultural chemicals, and which is represented by the formula [3] [in the formula R represents a lower alkyl group of a carbon and * represents an asymmetric carbon], or its salt by subjecting an optically active imine represented by the formula [1] to an asymmetric reduction under hydrogen atmosphere using a metal catalyst of Group VIII to convert it into an optically active secondary amine represented by the formula [2] and then by subjecting the secondary amine or its salt to hydrogenolysis.[Chem. 23]

REFERENCES:
patent: 5939588 (1999-08-01), Soloshonok et al.
patent: 10-182578 (1998-07-01), None
patent: 2002-30048 (2002-01-01), None
Database CAPLUS on STN, Acc. No. 1977:452888, Pirkle et al., Journal of Organic Chemistry (1977), 42(14), p. 2436-2439 (abstract).
International Search Report dated Aug. 24, 2004 based on International Application No. PCT/JP2004/007955, filed Jun. 8, 2004.
Török, Bèla et al., “Synthesis of Chiral Trifluoromethylated Amines by Palladium-Catalyzed Diastereoselective Hydrogenation-Hydrogenolysis Approach”, Adv. Synth. Catal. 2003, 345, No. 1&2, pp. 165-168; XP-002989156.
Pirkle, W.H. et al., “Design of Chiral Derivatizing Agents for the Chromatographic Resolution of Optical Isomers. Asymmetric Synthesis of Some Chiral Fluoroalkylated Amines”, J. Org. Chem., vol. 42, No. 14, 1977, pp. 2436-2439; XP-002989157.
Soloshonok Vadim et al., “Highly Enantioselective Transfer of Chirality from a Less to a More Configurationally Unstable Stereogenic Center. A Practical Asymmetric Synthesis of (Fluoroalkyl) amines via Biomimetic Transamination”, J. Org. Chem. 1997, 62, pp. 3030-3031; XP-002291600.
European Search Reprot dated Nov. 27, 2007 (three (3) pages).

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