HCID 86639072, compound → HCID 59190397, compound

Participants

Reaction Steps

A stirred solution of tert-butyl (S)-1-(4-bromophenyl)ethyl(4-(tert-butylsulfinylimino)-4-phenylbutyl)carbamate (926 mg, 1.69 mmol) in dry THF (25 mL) was cooled in a dry ice/i-PrOH bath and 1 M allylmagnesium bromide (4.2 mL, 4.2 mmol) was added dropwise over 2 min The mixture was stirred in the cooling bath for 3 h, diluted with satd aq NH4Cl (50 mL) and extracted with EtOAc (2×50 mL). The combined EtOAc extracts were washed with brine (15 mL), dried over Na2SO4 and concentrated to afford tert-butyl (S)-1-(4-bromophenyl)ethyl(4-(1,1-dimethylethylsulfinamido)-4-phenylhept-6-enyl)carbamate (990 mg, 99%) as an oil. LC-MS Method 1 tR=2.47 min, m/z=593, 591.

Provenance & Evidence