Process for the preparation of substituted keto-enamines

Details Process for the preparation of substituted keto-enamines Process for the preparation of substituted keto-enamines

1997-05-30

1999-08-03

Huang, Evelyn Mei

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

Organic compounds

Amino nitrogen containing

546 99, 548482, 558388, 558404, 558408, 558311, 564342, 564343, C07C21122, C07C21128, C07C25500

Patent

active

059327669

ABSTRACT:
The present invention discloses a process for the preparation of a compound having formula 4: ##STR1## The process comprises the step of reacting an enolate having the formula: ##STR2## with a Grignard reagent. The enolate salt is formed in situ from the reaction of a protected ester wherein M is an alkali metal. R.sub.6 and R.sub.7 are each hydrogen or are independently selected from ##STR3## wherein R.sub.a and R.sub.b are independently selected from hydrogen, lower alkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, lower alkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR4## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from lower alkyl, trifluoromethyl, alkoxy and halo. Alternatively, R.sub.6 is as defined above and R.sub.7 is R.sub.12 OC(O)-- wherein R.sub.12 is benzyl; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded form ##STR5## wherein R.sub.f, R.sub.g, R.sub.h and R.sub.i are independently selected from hydrogen, lower alkyl, alkoxy, halogen and trifluoromethyl.

REFERENCES:
patent: 5491253 (1996-02-01), Stuk et al.
patent: 5541206 (1996-07-01), Kempf et al.
patent: 5688985 (1997-11-01), Fujihara
Stuk et al., J. Org. Chem. 59 4040-4041 (1994).
Brillon, et al., J. Org. Chem 57 1838-1842 (1992).
Ghosh et al., J. Org. Chem 58 1025-1029 (1993).

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