Asymmetric synthesis of phenylisopropylamines

Details Asymmetric synthesis of phenylisopropylamines Asymmetric synthesis of phenylisopropylamines

1973-07-23

1976-12-28

Hines, Robert V.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260559R, 260566F, 260592, 260612D, C07C 8728

Patent

active

040001970

ABSTRACT:
The synthesis of enantiomers of a series of methoxy- and alkyl- substituted phenylisopropylamines is described. The synthesis comprises reducing the imines, formed by the reaction of appropriate phenylacetones with either (+)- or (-)-.alpha.-methylbenzylamine, by low-pressure reduction techniques, and subsequently subjecting the optically active N-(.alpha.-phenethyl)phenylisopropylamine derivative to hydrogenolysis. The hydrogenolysis products are characterized by enantiomeric purities in the range of 96 - 99%. Yields of products are approximately 60%.

REFERENCES:
patent: 2146475 (1939-02-01), Hildebrandt
patent: 2223686 (1940-12-01), Hildebrandt
patent: 3689524 (1972-09-01), Jack et al.
Weinges et al.; "Chem. Ztg. Chem. App.", vol. 94, No. 19, p. 728 (1970).
Adams et al., "Organic Reactions", vol. IV, pp. 181-182, 189-195, 223 and 236, (1948).

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