Dimethylformamide → HCID 58055032, compound

Participants

Reaction Steps

To a solution of tert-butyl (3R,4S)-3-hydroxy-4-(tert-butyldimethylsilyl)oxy-3-(prop-2-en-1-yl)pyrrolidine-1-carboxylate (550 mg) in DMF (10 mL) was added iodemethane (2.2 g) at 0° C. After 10 min, 60% NaH in oil (62 mg) was added, and the mixture was stirred for 1 hour at room temperature. The reaction was quenched with saturated aqueous NH4Cl and the mixture was extracted with Et2O. The extract was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜50/50) to give tert-butyl (3R,4S)-4-(tert-butyldimethylsilyl)oxy-3-methoxy-3-(prop-2-en-1-yl)pyrrolidine-1-carboxylate as a pale yellow foam.

Provenance & Evidence