Borane;tetrahydrofuran → HCID 58237949, compound

Participants

Reaction Steps

To a solution of (S)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)piperidin-2-one (70 mg, 0.169 mmol) in THF (5 mL) was added BH3/THF (0.6 mL, 1 M) at 0° C. under nitrogen atmosphere. The mixture was stirred for 2 h, and the reaction was quenched with water. Aqueous NaOH solution (1 M, 2 mL) and H2O2 (1 mL□30%) were added to the above mixture, and the resulting mixture was stirred for 1 h. The mixture was extracted with EtOAc, and the combined organic phase was concentrated to give the crude product, which was purified by preparative HPLC to give (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-4-(3-hydroxypropyl)piperidin-2-one (30 mg, 41%). 1H NMR (CDCl3): δ 1.36 (m, 1H), 1.52 (m, 1H), 1.72 (m, 2H), 1.89 (m, 1H), 1.98 (m, 1H), 2.21 (m, 1H), 2.44 (m, 1H), 2.92 (m, 1H), 3.01 (m, 1H), 3.44 (m, 2H), 5.92 (m, 2H), 6.73 (m, 2H), 6.91 (m, 2H), 7.14 (m, 4H).

Provenance & Evidence