Boron trichloride methylene chloride → (3R,6R,7aS)-4-(3-tert-Butyl-6-hydroxy-1-oxo-tetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-naphthalene-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Compound 33C (94.4 mg, 0.2 mmol) was dissolved in dry CH2Cl2 (5.0 ml), cooled to −75° C., treated with 1.0 M BCl3/CH2Cl2 (1.2 ml, 1.2 mmol) and stirred at −75° C. for 1.5 hr. The reaction mixture was quenched with ice-water (3.4 ml), warmed to room temperature, stirred for 5 min then extracted with CH2Cl2 (50 ml). The organic phase was washed with water (3.4 ml) and brine (3.4 ml) and dried (Na2SO4). Purification using automated flash chromatography (35 g silica gel column, EtOAc/hexane gradient) gave the title compound as a white solid (34.7 mg, 49.6%), m.p. 155-157° C. MS (ES): m/z 350 [M+1]+.

Provenance & Evidence