Acetic Acid → [(3R,4S)-3-[(R)-1-(5-Chloro-pyridin-2-yloxy)-2-hydroxy-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(2-methyl-pyrimidin-5-yl)-methanone

Participants

Reaction Steps

To a solution of [(3R,4S)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(6-methyl-pyridazin-4-yl)-methanone (0.074 g, 0.119 mmol) dissolved in THF (4 mL) was added 0.014 mL (0.24 mmol) of acetic acid and 0.119 mL of TBAF (1.0M in THF). The reaction mixture was stirred over night at room temperature. The mixture was diluted with ethyl acetate and washed with water and aq. sodium bicarbonate solution subsequently. The separated organic phase was dried over sodium sulfate and concentrated in vaccuo after filtration. The residue was purified by TLC (SiO2, MeOH/DCM, 1:10) yielded 55 mg (91%) of the title compound as a light yellow oil. ES-MS m/e: 507.1 (M+H+).

Provenance & Evidence