Stereoselective reduction of carbonyl compounds

C - Chemistry – Metallurgy – 07 – C

Patent

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Details

C07C 271/16 (2006.01) C07B 53/00 (2006.01) C07C 29/143 (2006.01) C07C 269/06 (2006.01) C07C 319/20 (2006.01) C07C 323/43 (2006.01) C07D 207/333 (2006.01) C07D 213/30 (2006.01) C07D 307/42 (2006.01) C07D 333/16 (2006.01) C07C 323/41 (2006.01)

Patent

CA 2273643

A process for the stereoselective reduction via a Meerwein-Ponndorf-Verley (MPV) reaction, of a carbonyl compound to the corresponding alcohol. A preferred starting carbonyl compound is a ketone compound wherein the carbonyl carbon is prochiral. The starting carbonyl compound is contacted with an MPV mediator such as aluminum isopropoxide. The reaction is conducted under mild conditions, e.g. temperatures of about 50°C or less, for less than four hours, and is capable of producing an excess (about 90% to about 97% or more) of a desired optically active chiral alcohol. The mild reaction conditions preserve the optical orientation of other asymmetric centers in the carbonyl compound starting material. Steroselective and stereospecific reactions for producing desired optically active alcohols are useful for the preparation of intermediate and final pharmaceutical products.

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