Methyl iodide → HCID 51354610, compound

Participants

Reaction Steps

To 1,1-dimethylethyl[(3R,5R)-5-methyl-1-(phenylmethyl)-3-piperidinyl]carbamate (196 mg, 0.644 mmol) in DMF (3 mL) was added NaH (38.6 mg, 0.966 mmol), and the resulting mixture was vigorously stirred for 30 minutes. CH3I (0.044 mL, 0.708 mmol) was added, and the reaction mixture was stirred for 3 hours at room temperature. Saturated aqueous NaHCO3 was added carefully (˜5 mL: initial vigorous bubbling), and the resulting mixture was poured onto water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% Hexane to 30% EtOAc/Hexane) afforded the title compound (162 mg) as a colorless oil. LC-MS (ES) m/z=319 [M+H]+.

Provenance & Evidence