Methanol → HCID 67248100, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 15B (168 mg, 0.435 mmol) in tetrahydrofuran (1.5 mL) was added borane in tetrahydrofuran (1.74 mL, 1 M solution). The resulting mixture was heated to 80° C. overnight. Methanol was then added, and the mixture was heated at 80° C. for 1 hour to destroy excess borane. The reaction was then cooled to room temperature and 1 M HCl was added. The mixture was allowed to stir for another 30 minutes. Aqueous sodium bicarbonate was slowly added to the mixture until the solution was basic (pH=8). Ethyl acetate was then added, and the water layer was separated and washed two times with additional ethyl acetate. The organic layers thus obtained were combined and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 0% to 30% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 6.88 (s, 1H), 6.70 (s, 1H), 5.75 (d, J=5.55 Hz, 1H), 3.61-3.79 (m, 1H), 3.36-3.58 (m, 2H), 2.95-3.23 (m, 5H), 2.82-2.94 (m, 1H), 1.80-1.97 (m, 1H), 1.56-1.74 (m, 1H), 1.41 (s, 9H); MS (DCI+) m/z 372.2 (M+H)+.

Provenance & Evidence