Method for introducing a 1,2 double bond into azasteroids

Details Method for introducing a 1,2 double bond into azasteroids Method for introducing a 1,2 double bond into azasteroids

1989-11-13

1991-06-04

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

A61K 31395

Patent

active

050215752

ABSTRACT:
A process for introducing a 1,2 double bond into a compound of the formula ##STR1## which comprises the process of (a) treating the compound of formula I with oxalyl chloride; (b) brominating the product of step (a) followed by in situ dehydrobromination; (c) deprotecting the product of step (b) to yield the .alpha. and .beta. isomers; (d) dehydrobrominating the product of step (c), which results in the introduction of a double bond at the 1,2 position.

REFERENCES:
patent: 4220775 (1985-09-01), Rasmusson et al.
patent: 4377584 (1983-03-01), Rasmusson
Bhattacharya et al., JACS vol. 110, 3318(1988).
Back J. Org. Chem. vol. 46, 1442-1446(1981).
Rasmusson et al., J. Med. Chem. vol. 29, 2298-2315(1986).
Magnus et al., JACS, vol. 108, pp. 222-227(1986).
Back, T. G., J.C.S. Chem. Comm. 278-279(1978).

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