Sodium Sulfide → HCID 21849647, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of cis-1-(phenylmethyl)-3,4-di(methylsulfonyloxy)methylpyrrolidine (9.2 g, mmol), in dry DMSO (48 mL) was added anhydrous sodium sulfide (5.7 g, 73.3 mmol). The dark reaction mixture was heated at 120° C. for 18 h. The cooled reaction mixture was poured into ice H2O (150 mL). The resulting mixture was washed with ether (3×200 mL). The combined organics were dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash chromatography using ethyl acetate as the eluent to afford 4.2 g (19.1 mmol, 78%) of the desired product as a thick yellow oil. HRMS (EI) calcd for C13H17NS 219.1082, found 219.1080. Anal. calcd for C13H17NS: C, 71.19; H, 7.81; N, 6.39. Found: C, 70.82; H, 7.83; N, 6.35.

Provenance & Evidence