Methanol → HCID 57516630, compound

Participants

Reaction Conditions

Reaction Steps

3-(3-Bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-2,4-dione (4.25 g, 16.0 mmol) was suspended in 80 mL of THF. Borane dimethyl sulfide complex (14.2 mL of a 10.1 M solution) was added and the reaction was heated at 50° C. for 1 h. The reaction was cooled in an ice bath. Methanol (65 mL) was slowly added, followed by 150 mL of water. This mixture was extracted with EtOAc (2×) and the combined organics were dried over MgSO4 and concentrated. The residue was taken up in dichloromethane and the resulting suspension was filtered. The filtrate was concentrated and the residue was purified by SiO2 chromatography using a gradient of 0% to 20% ethyl acetate/heptane to afford 3.63 g (95%) of 3-(3-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane as a white solid.

Provenance & Evidence