O-Benzylhydroxylamine → 2-(Benzyloxyaminomethyl)-4-methylpentanoic acid

Participants

Reaction Steps

A solution of 4-methyl-2-methylenepentanoic acid (3.5 g) and O-benzylhydroxylamine were heated at 120° for 8 h. The reaction mixture was then partitioned between 50 mL of 1.0N NaOH and 50 mL of diethyl ether. The aqueous portion was separated, acidified to pH 3 with 10% HCl and washed with 50 mL of ether. Ion exchange chromatography (Dowex-50W) eluting with 20% pyridine/water gave 2-(benzyloxyaminomethyl)-4-methylpentanoic acid.

Provenance & Evidence