Methanol → HCID 67001762, compound

Participants

Reaction Steps

A solution of alane-N,N-dimethylethylamine complex (0.5 M in toluene, 5.0 mL, 2.50 mmol) was added dropwise over 2 minutes to a solution of the product of Example 64A (506 mg, 1.59 mmol) in dry tetrahydrofuran (22 mL). The reaction was stirred at room temperature for 5 hours. Additional portions of alane-N,N-dimethylethylamine complex (0.5 M in toluene, 5.0 mL, 2.50 mmol) were added after 1 hour, and again after 4 hours. Methanol (10 mL) was added, followed after 10 minutes by water (20 mL) and 25% NaOH (3 mL). The mixture was stirred for 10 minutes, and the aqueous layer was separated and extracted with ethyl acetate (30 mL). The combined organic phases were washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by chromatography (SiO2, eluted with ethyl acetate-ethanol, 90:10) to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 1.73-1.88 (m, 1H), 1.90-2.07 (m, 1H), 3.17-3.40 (m, 2H), 3.40-3.83 (m, 7H), 6.67 (dd, J=7.8, 4.8 Hz, 1H), 6.76 (d, J=7.8 Hz, 1H), 7.75 (dd, J=4.7, 1.7 Hz, 1H); MS (DCI) m/z 305 (M+H)+.

Provenance & Evidence