Potassium bis(trimethylsilyl)amide → HCID 18723515, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 0.08 g (0.22 mmol) of methyltriphenyl phosphonium bromide (Ph3PCH3Br) in 4 mL of THF at rt was added 0.36 mL of potassium bis(trimethylsilyl)amide and the reaction mixture was stirred for 30 min. The reaction mixture was cooled to 0° C. and to it was added a solution of 0.04 g (0.089 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-formylpyrrolidine in 2 mL of THF. The reaction mixture was warmed to rt and stirred for 1.2 h. The reaction mixture was filtered through a thin pad of silica eluting with acetone:hexanes, 1:2, then concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:2) to give the title compound. Mass Spectrum (ESI) m/e=444 (M+1).

Provenance & Evidence