Methanol → HCID 67606706, compound

Participants

Reaction Steps

A solution of ester 76 (2.7 g, 6.7 mmol) in THF (15 mL) was cooled to 0° C. and treated with LiBH4 (10 mL, 2M in THF). After 3 h, the solution was slowly treated with MeOH followed by H2O. The solution was then concentrated and diluted with EtOAc. The solution was slowly treated with 1M HCl until gas generation ceased. The solution was extracted with EtOAc, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was absorbed onto SiO2 and purified by flash chromatography (1:1 hexane/EtOAc to 1:2 hexane/EtOAc) to afford alcohol 77 (1.9 g, 75%) as a light yellow-colored oil. 1H NMR (CDCl3, 300 MHz): δ7.39-7.27 (m, 5H), 5.13-5.09 (m, 2H), 4.43-4.41 (m, 1H), 4.13-4.08 (m, 2H), 3.70-3.29 (m, 6H), 2.48-2.46 (m, 1H), 2.53-2.05 (m, 1H), 2.03-1.99 (m, 1H), 1.48 (s, 9H) ppm. Mass spectrum, m/z [377.5] (M+H)+.

Provenance & Evidence