Process for making 17-beta alkanoyl 3-oxo-4-aza-5-.alpha.-andros

Details Process for making 17-beta alkanoyl 3-oxo-4-aza-5-.alpha.-andros Process for making 17-beta alkanoyl 3-oxo-4-aza-5-.alpha.-andros

1990-09-24

1991-10-29

Shah, Mukund J.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514859, C07J 7300, A61K 3158

Patent

active

050618032

ABSTRACT:
Disclosed is a new process for making 17-beta branched alkanoyl-3-oxo-4-aza-5-.alpha.-androst-1-enes, agents for treating benign prostatic hypertrophy (BPH), by reacting methyl 3-oxo-4-aza-5-.alpha.-androst-1-ene-17-beta carboxylate with isobutylmagnesium bromide in the novel presence of the hexamethyldisilazane (HMDS). Use of the HMDS results in higher yield and less by-products as opposed to the standard Grignard reaction in the absence of HMDS.

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patent: 4760071 (1988-07-01), Rasmusson et al.
patent: 4859681 (1989-08-01), Rasmusson et al.
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Synthesis, Nov. 1980, pp. 878-890.
Helv. Chim. Acta, vol. 69 (1986), pp. 228-235.
J. Med. Chem., vol. 29, No. 11, pp. 2298-2315 by Rasmusson et al.
"Protective Groups on Organic Synthesis"by Theodora W. Greene, 1981, Wiley, New York, pp. 40-41.

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