Water → HCID 68109544, compound

Participants

Reaction Steps

The product obtained from step A (269 mg, 0.50 mmol) was dissolved in ethanol (10 mL) at 0° C. Lithium borohydride (220 mg, 10.0 mmol) was added slowly and the reaction mixture was stirred at ambient temperature for 2 h. Water (10 mL) was added and the mixture was extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over MgSO4, filtered, and the filtrate concentrated in vacuo. Purification by flash column chromatography (SiO2, 9:1 to 7:3 hexanes/ethyl acetate) afforded (6-chloro-2-(4-methoxybenzyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-1-yl)methanol (149 mg, 60%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.05-7.94 (m, 3H), 7.86-7.83 (m, 1H), 7.57-7.48 (m, 3H), 7.26-7.21 (m, 3H), 6.92-6.87 (m, 2H), 4.02-3.98 (m, 1H), 3.82 (s, 3H), 3.83-3.80 (m, 1H), 3.72 (s, 2H), 3.64-3.57 (m, 1H), 3.29-3.19 (m, 1H), 3.12-2.98 (m, 2H), 2.68-2.60 (m, 1H).

Provenance & Evidence