Methyl 1-(4-bromophenyl)cyclopropyl(3-oxo-3-phenylpropyl)carbamate → HCID 66870054, compound

Participants

Reaction Steps

A solution of methyl 1-(4-bromophenyl)cyclopropyl(3-oxo-3-phenylpropyl)carbamate (127 mg, 0.316 mmol) in dry THF (10 mL) was cooled to −78° C. A solution of 0.5M 2-methylallylmagnesium chloride in THF (1.9 mL, 3 equiv) was added. After 10min, the reaction mixture was warmed to rt slowly and stirred for 1 h. LC-MS found the reaction was complete. The mixture was quenched with satd aq NH4Cl (3 mL), diluted with ether (40 mL), washed with 1% aq HCl (8 mL), satd aq NaHCO3 (7 mL), and brine (5 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 12-g silica gel column, eluted with a 0˜30% EtOAc in hexanes gradient, to afford methyl 1-(4-bromophenyl)cyclopropyl(3-hydroxy-5-methyl-3-phenylhex-5-enyl)carbamate (58.8 mg, 41%).

Provenance & Evidence