Methanol → HCID 69600997, compound

Participants

Reaction Steps

To a solution of 3-7 (0.4 g, 1.0 mmol) in 12 mL 5:1 MeOH:acetic acid was added sodium cyanoborohydride (100 mg, 1.4 mmol) and the resulting solution was stirred overnight at room temperature. The solution was quenched with water and was concentrated in vacuo. The concentrate was extracted with ethyl acetate and washed with 2M Na2CO3 and then brine, after which it was dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 60% ethyl acetate/hexanes to yield 400 mg of 3-8 as a colorless oil. Data shown is for the major diastereomer. 1H NMR (400 MHz, CDCl3): δ 7.35–7.21 (m, 5H), 5.84 (dd, 1H), 5.66 (dd, 1H), 4.46 (q, 1H), 4.23 (q, 1H), 4.14 (q, 2H), 3.68–3.37 (m, 2H), 2.97 (dd, 1H), 2.88 (m, 2H), 2.78 (m, 1H), 2.30 (t, 2H), 1.64–1.30 (m, 8H), 1.27 (t, 3H); MS (+ESI): m/z 406.2 (M+1)+.

Provenance & Evidence