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

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.

1. filtrationThe reaction mixture was filtered through Arbocel®
2. washwashed with ethanol (20 ml)
3. customThe liquor was evaporated under reduced pressure
4. customthe residue was partitioned between dichloromethane (50 ml) and water (50 ml)
5. customThe organic layer was removed
6. extractionthe aqueous phase was extracted with more dichloromethane (50 ml)
7. customThe water layer was evaporated under reduced pressure
8. customto give a yellow solid
9. customThe product was purified by ion exchange chromatography on Dowex 50 WX8 resin
10. washeluting with 0.88 aqueous ammonia:water (2:98 to 14:86)

ORD record

ord-a19bfdc150444d6d8b4050c9e8092cfc

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612226B2