Benzyl Chloride → HCID 22601252, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure 12, to a cold (0° C.), stirred solution of the alcohol (23) (58 mg, 1 equiv.) in DMF (5 mL) was added NaH (60% in oil, 31 mg, 1.5 equiv.). The suspension was stirred at 0° C. for 40 minutes followed by the addition of the benzyl chloride (120 uL, 2 equiv.). The suspension was warmed to rt and stirred for 6 h. MeOH was added followed by sat. aq. NH4Cl. The aqueous phase was extracted with EtOAc (3×) and the combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (25% EtOAc in hexane) to afford the desired benzyl ether 3-(benzyloxy)-1-cyanopyrrolidine (24).

Provenance & Evidence