Diisopropylethylamine → 2-{(RS)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3RS,4SR)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-chloro-pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[(RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-pyridine (7A-1) 108 mg (0.182 mmol) dissolved in toluene (2 mL) was added 0.059 mL (0.547 mmol) of 1-chloroethyl chloroformate and 0.093 mL (0.547 mmol) of Hunig base subsequently, and the mixture was heated at 100° C. for 40 minutes, then concentrated in vaccuo. The residue was dissolved in methanol (5 mL) and heated at reflux temperature for 30 minutes. The mixture was concentrated in vacuo and diluted with ethyl acetate, then washed with aq. sodium bicarbonate solution twice. The combined organic layers was dried over sodium sulfate and concentrated in vaccuo after filtration. The residue was purified by silica gel column chromatography (DCM/MeOH 10:1 to 4:1) yielding 0.047 g (51%) of the title compound as a light brown oil. ES-MS m/e: 501.2 (M+H+).

Provenance & Evidence