Optically active (R)-1-(4-trifluoromethylphenyl)ethylamine

Details Optically active (R)-1-(4-trifluoromethylphenyl)ethylamine Optically active (R)-1-(4-trifluoromethylphenyl)ethylamine

2006-07-25

2006-07-25

Davis, Brian (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C564S272000, C564S392000

Reexamination Certificate

active

07081551

ABSTRACT:
Optically active (R)-1-(4-trifluoromethylphenyl)ethylamine is a novel compound as an important intermediate for medicines and agricultural chemicals. This compound can be obtained with high optical purity and high yield by a process including the steps of (a) a dehydrocondensation of 4′-(trifluoromethyl)acetophenone and an optically active (R)-1-phenylethylamine to obtain an optically active imine; (b) asymmetrically reducing the imine into an optically active secondary amine; (c) reacting the amine with an organic acid (phthalic acid or benzenesulfonic acid), thereby obtaining a product that is a phthalate of or benzenesulfonate of the amine; (d) subjecting the product of the step (c) to a hydrogenolysis, thereby obtaining a product that is a phthalate of or benzenesuilfonate of optically active (R)-1-(4-trifluoromethylphenyl)ethylamine; and (e) neutralizing the product of the step (d) into the optically active (R)-1-(4-trifluoromethylphenyl)ethylamine.

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Smith et al., “Optically Active Amines. 31.1Spectral Observations on the Substituted Benzene Chromophore2”,J. Am. Chem. Soc., vol. 105 (1983), pp. 1578-1584.

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