Method of preparing .alpha.-d-phenylalkylbenzyl carbinol

Details Method of preparing .alpha.-d-phenylalkylbenzyl carbinol Method of preparing .alpha.-d-phenylalkylbenzyl carbinol

1992-10-08

1994-02-08

Hollrah, Glennon H.

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

Organic compounds

Amino nitrogen containing

564356, 564425, 568807, C07C23506

Patent

active

052849759

ABSTRACT:
A method of preparing an .alpha.-d-phenylalkylbenzyl carbinol by the reaction of a phenylbenzyl ketone with an alkali metal enolate of an amide to form an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol, wherein the carbinol so produced possesses analgesic activity. In an embodiment of the invention, a phenylbenzyl ketone is reacted with an alkali metal enolate of an amide to form an aldol adduct, which is reacted with an alkali metal salt of a secondary amine to form a dianion; the dianion is alkylated with an alkyl halide to form an .alpha.-isomer of an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol possessing analgesic activity.

REFERENCES:
G. Frater, Tetrahedron Letters, 22: pp. 425-427, 1981.
D. Seebach et al., Organic Synthesis, Coll. vol. 7, pp. 153-159. (1990).
B. McEwan, Propoxyphene Hydrochloride, pp. 302-317. (1972).
Tetrahedron Letters, vol. 24, No. 47, (1983) pp. 5233-5236.
Tetrahedron Letters, vol. 27, No. 30, (1986) pp. 3511-3514.
Tetrahedron Letters, vol. 28, No. 9 (1987) pp. 985-988.
March, J. Advanced Organic Chemistry (1992) John Wiley & Sons, pp. 896-898.

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