Diisopropylethylamine → 6-{(SR)-1-[(3RS,4SR)-4-(4-Cyano-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-{(SR)-1-[(3RS,4SR)-1-benzyl-4-(4-cyano-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile (VI-B-5) 380 mg (0.93 mmol) dissolved in toluene (10 mL) were added 0.30 mL (2.79 mmol) of 1-chloroethyl chloroformate and 0.47 mL (2.79 mmol) of Hunig's base. The reaction mixture was heated at 100° C. for one hour. After cooling down to RT, volatiles were removed under vacuo and the crude was dissolved in MeOH (10 mL). The reaction mixture was heated at 85° C. for 30 minutes and after cooling down to RT, volatiles were removed under vacuo and the residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1) yielded 105 mg (35%) of the title compound as a light yellow oil. ES-MS m/e: 319.2 (M+H+).

Provenance & Evidence