Trifluoroacetic acid → HCID 9899272, compound

Participants

Reaction Steps

Following general procedure 12, to a cold (0° C.), stirred solution of the alcohol (26) (188 mg, 1 equiv.) in DMF (9 mL) was added NaH (60% in oil, 56 mg, 1.5 equiv.). The suspension was stirred at 0° C. for 40 minutes followed by the addition of the benzyl chloride (215 uL, 2 equiv.). The suspension was warmed to rt and stirred for 16 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 (20% EtOAc in hexane) to afford the desired benzyl ether (27). The N-Boc group of the benzyl ether (27) was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 50% EtOAc in hexane) to afford the desired product 3-[(benzyloxy)methyl]-1-cyanopyrrolidine (28).

Provenance & Evidence