Tetrahydrofuran → HCID 58109684, compound

Participants

Reaction Steps

To a solution of (R)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (260 mg, 0.536 mmol) in THF (3 mL) was added BH3 THF (1.6 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 (1 mol/L, 2 mL) and H2O2 (1 mL) were 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 crude (R)-3-((S)-1-(4-(2-hydroxyethyl)phenyl)ethyl)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-1,3-oxazinan-2-one (260 mg, 96%), which was used for the next step without purification. 1H NMR (CDCl3): δ=1.32 (m, 2H), 1.41 (d, 3H), 1.89 (m, 2H), 2.12 (m, 1H), 2.22 (m, 2H), 2.68 (m, 1H), 2.81 (m, 1H), 3.27 (m, 2H), 3.72 (s, 3H), 4.26 (s, 2H), 5.53 (q, 1H), 6.71-6.88 (m, 5H), 7.13 (m, 2H), 7.26 (m, 4H).

Provenance & Evidence