(3S,5S)-3-(cyclobutylmethyl)-3-methyl-5-phenylmorpholin-2-one → (2S)-2-amino-3-cyclobutyl-2-methylpropanoic acid

Participants

Reaction Steps

Pearlman's catalyst (0.5 g) was added to a solution of (3S,5S)-3-(cyclobutylmethyl)-3-methyl-5-phenylmorpholin-2-one (0.445 g, 1.7 mmol, Preparation 5) in ethanol (15 ml), water (2 ml) and trifluoroacetic acid (0.5 ml). The reaction was stirred under hydrogen gas (414 kPa, 60 psi) at room temperature for 24 hours. The reaction mixture was filtered through Arbocel® and washed with ethanol (20 ml). The liquor was evaporated under reduced pressure and the residue was partitioned between dichloromethane (50 ml) and water (50 ml). The organic layer was removed and the aqueous phase was extracted with more dichloromethane (50 ml). The water layer was evaporated under reduced pressure to give a yellow solid. The product was purified by ion exchange chromatography on Dowex 50 WX8 resin, eluting with 0.88 aqueous ammonia:water (2:98 to 14:86) to give the title compound (0.034 g) as a white solid.

Provenance & Evidence