Borane;tetrahydrofuran → HCID 44194573, compound

Participants

Reaction Steps

To a solution of 5-(4-((S)-1-((S)-4-allyl-4-(4-fluorophenyl)-2-oxopiperidin-1-yl)ethyl)phenyl)-1-methylpyridin-2(1H)-one (45 mg, 0.10 mmol) in THF (3 mL) was added BH3/THF (0.3 mL, 1 M) at 0° C. under nitrogen atmosphere. The mixture was stirred for 2 h. The reaction was quenched with water. Aqueous NaOH solution (1 M, 0.6 mL) and H2O2 (0.3 mL□30%) were added to the above mixture. 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 5-(4-((S)-1-((S)-4-(4-fluorophenyl)-4-(3-hydroxypropyl)-2-oxopiperidin-1-yl)ethyl)phenyl)-1-methylpyridin-2(1H)-one (1.0 mg, 2%). LC-MS Method 2, tR=1.63 min, m/z=463.1. 1H NMR (CDCl3): δ1.42 (t, 3H), 1.69 (m, 2H), 1.92 (m, 1H), 2.01 (m, 1H), 2.22 (m, 2H), 2.44 (d, 2H), 2.99 (m, 3H), 3.36 (m, 1H), 3.42 (t, 2H), 3.59 (s, 3H), 3.60 (m, 1H), 3.84 (m, 1H), 6.01 (q, 1H), 6.61 (d, 1H) □ 6.89 (m, 4H), 7.14 (m, 4H), 7.33 (d, 1H), 7.49 (m, 1H).

Provenance & Evidence