(6R, 7S)-2,2-dimethyl-7-(1-methoxy-1-methylethyl)-1-aza-3-oxabicyclo[4.2.0]octan-8-one → (3S, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of (6R, 7S)-2,2-dimethyl-7-(1-methoxy-1-methylethyl)-1-aza-3-oxabicyclo[4.2.0]octan-8-one (142.3 mg) in a mixture of acetic acid (2.28 ml) and water (0.57 ml) was heated at 65° C. for 1.5 hours. The mixture was cooled to ambient temperature and then evaporated in vacuo. Xylene was added to the residue and the resultant suspension was evaporated in vacuo. The residue was dissolved in a mixture of methanol and xylene, and the resultant solution was evaporated in vacuo. This operation was repeated once and the residue was chromatographed on silica gel (1.5 g) eluting with a mixture of methylene chloride and acetone (10:1 to 1:1) to give (3S, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one (111.3 mg).

Provenance & Evidence