Benzyl Bromide → HCID 54067774, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (0.10 mL, 1.45M in hexane, 0.14 mmol) was added to a solution of (R)-5-benzyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole (Example 7e, 24 mg, 0.052 mmol) in THF (2 mL) at -78° C.; the temperature was raised to 0° C. and the mixture was stirred for 20 min. After recooling to -78° C., benzyl bromide (18 μL, 0.15 mmol) was added and the mixture was stirred for 1 h at 78° C.; then 15 min. without cooling prior to quenching with water and extraction with ethyl acetate. The organic layer was washed sequentially with water and brine, and dried over sodium sulfate. Palladium on carbon (10%) was added to a solution of the crude product in methanol (2 mL) and the mixture was stirred under an atmosphere of hydrogen for 1.5 h. Removal of the catalyst by filtration followed by flash chromatography (silica gel, 0-10% 2M methanolic ammonia in dichloromethane) yielded (R)-2-benzyl-5-hydroxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole (12.5 mg, 40%; HRMS-FAB+ for C27H28N2O3S calculated MH+ :461.18988; found MH+ :461.18724).

Provenance & Evidence