Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid

Abstract

The present invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid which comprises condensing isovaleraldehyde with an alkyl cyanoacetate to form a 2-cyano-5-methylhex-2-enoic acid alkyl ester; reacting the 2-cyano-5-methylhex-2-enoic acid alkyl ester with a dialkyl malonate to form 3-isobutylglutaric acid; forming the anhydride of 3-isobutylglutaric acid; reacting the anhydride with ammonia to form (.+-.)-3-(carbamoylmethyl)-5-methylhexanoic acid; reacting (.+-.)-3-(carbamoylmethyl)-5-methylhexanoic acid with (R)-(+)-.alpha.-phenylethylamine to obtain the (R)-(+)-.alpha.-phenylethylamine salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid; combining the salt with an acid to obtain (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid; and reacting the (R)-(-)-3-carbamoylmethyl)-5-methylhexanoic acid with a Hofmann reagent to obtain (S)-(+)-3-(amino-methyl)-5-methylhexanoic acid.

Dependencies are inferred from the claim text.