Triethylsilane → 3-(3,4-Difluorophenyl)pyrrolidin-3-ol

Participants

Reaction Steps

A mixture of enantiomer E1 of 1-benzyl-3-(3,4-difluorophenyl)pyrrolidin-3-ol (0.81 g, 2.8 mmol), methanol (15 mL) and palladium on carbon (160 mg) was purged with nitrogen. Triethyl silane (6.5 g, 56 mmol) was added drop wise and the resulting mixture was stirred at ambient temperature for 3 h after which the mixture was filtrated over celite and evaporated. Methanol (15 mL) and palladium on carbon (160 mg) was added and the mixture was purged with nitrogen. Triethyl silane (6.5 g, 56 mmol) was added in 5 equal portions over 1.5 h and the resulting mixture was stirred at ambient temperature for 11.5 h. The mixture was filtrated over celite, evaporated and purified on a Biotage (solute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) to give the title compound (0.52 g). MS m/z (relative intensity, 70 eV) 199 (M+, bp), 141, (97), 127 (54), 114 (48), 113 (85).

Provenance & Evidence