Diisopropylethylamine → 2-{(S)-1-[(3R,4S)-4-(4-Chloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-fluoro-pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{(S)-1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-fluoro-pyridine 310 mg (0.75 mmol) dissolved in toluene (5 mL) were added 0.10 mL (0.98 mmol) of 1-chloroethyl chloroformate and 0.17 mL (0.98 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 230 mg (85%) of the title compound as a light yellow oil. ES-MS m/e: 321.3 (M+H+).

Provenance & Evidence