9-Oxobenzomorphan process

Details 9-Oxobenzomorphan process 9-Oxobenzomorphan process

1979-01-05

1980-11-18

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26032611R, C07D22126

Patent

active

042347319

ABSTRACT:
Improved processes for preparing 2'-alkoxy-2,5-di-substituted-9-oxo-6,7-benzomorphans from benz[e]indolines and synthesis of the benz[e]indoline intermediates are described. A representative example involves synthesis of 9b-allyl-8-methoxy-3-methyl-5,9b-dihydrobenz[e]indoline and bromination thereof to 9b-allyl-4-bromo-8-methoxy-2,4,5,9b-tetrahydro-1H-benz[e]indole methylbromide which is then hydrolyzed with a weak base such as ammonium bicarbonate to provide 5-allyl-2'-methoxy-2-methyl-9-oxo-6,7-benzomorphan.

REFERENCES:
patent: 3853889 (1974-12-01), Monkovic
patent: 3891657 (1975-06-01), Monkovic
patent: 3959290 (1976-05-01), Monkovic
Takeda et al., J. Org. Chem., vol. 37, pp. 2677-2679, (1972).
Murphy et al., J. Org. Chem., vol. 25, pp. 1386-1388, (1960).
Ahmed et al., Can. J. Chem., vol. 53, pp. 3276-3284, (1975).
Evans et al., J. Org. Chem., vol. 35, pp. 4122-4127, (1970).

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