Tetrahydrofuran → HCID 58109629, compound

Participants

Reaction Steps

To a solution of (S)-benzyl 3-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)piperidine-1-carboxylate (78 mg, 0.17 mmol) in THF (3 mL) was added BH3 THF (0.5 mL, 1 mol/L) at 0° C. under nitrogen atmosphere. The formed mixture was stirred for 2 h. The reaction was quenched with water. Then aqueous NaOH solution (3 mol/L, 0.2 mL) and H2O2 (30%, 0.4 mL) was added to the above mixture. The resulting mixture was stirred for 1.5 h. The mixture was extracted with EtOAc, and the combined organic phase was concentrated to give the crude product, which was purified by preparative TLC to give (S)-benzyl 3-((R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-2-oxo-1,3-oxazinan-3-yl)piperidine-1-carboxylate (15 mg, 20%). LC-MS Method 2 tR=1.299 min, m/z=493.1; 1H NMR (CDCl3): 1.12-1.35 (m, 2H), 1.46 (m, 1H), 1.57-1.28 (m, 4H), 1.82-1.98 (m, 2H), 2.11 (m, 1H), 2.23 (m, 1H), 2.46-2.73 (m, 3H), 3.11 (m, 1H), 3.50 (m, 2H), 3.86-4.03 (m, 1H), 5.06 (m, 2H), 6.89-7.01 (m, 2H), 7.16 (m, 2H), 7.23-7.33 (m, 4H).

Provenance & Evidence