Cyanogen Bromide → trans-1-Cyano-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

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Reaction Steps

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (300 mg, 0.94 mmol) and K2CO3 (195 mg, 1.5 mmol) in 5 mL of CH3CN at 0° C. was added cyanogen bromide (120 mg, 1.13 mmol). The solution was stirred for 24 hr, diluted with H2O and ethyl acetate, and washed with brine. The combined organic layers were dried over MgSO4, filtered and concentrated to an oil. Silica gel chromatography (3:1, hexanes:ethyl acetate) provided trans-1-cyano-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine as a white solid (166 mg, 51%).m.p. 78°-80° C. Anal. Calcd for C19H24N2O4 : C, 66.26; H, 7.02; N, 8.13. Found: C, 66.30; H, 7.04; N, 8.15.

Provenance & Evidence