Acetic Acid → HCID 59854982, compound

Participants

Reaction Steps

To a solution of 38 mg (0.085 mmol) of 10-2 in 1 mL of 1,2-dichloroethane was added 20 μL (0.34 mmol) of acetic acid, 25 μL (0.34 mmol) of acetone, and 27 mg (0.13 mmol) of Na(OAc)3BH. After stirring overnight, the reaction was partitioned between EtOAc and saturated aqueous NaHCO3, the organic phase was washed again with NaHCO3, H2O, brine, dried over Na2SO4, and concentrated by rotary evaporation. The residue was purified by reverse phase chromatography with 95:5 to 5:95 H2O/CH3CN (both with 0.1% TFA). The fractions were basified with NaHCO3 to provide 11-1 as a colorless film. Data for 11-1: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.3 (s, 1H), 5.3 (m, 1H), 4.95-4.8 (m, 2H), 4.6 (m, 1H), 4.45 (m, 1H), 4.1-4.0 (m, 2H), 3.2 (m, 1H), 3.15 (s, 3H), 3.0 (m, 1H), 2.8 (m, 1H), 2.45-2.25 (m, 3H), 1.75 (m, 1H), 1.1-1.0 (m, 6H) ppm. HRMS (ES) calc'd M+H for C27H32F3N3O2: 488.2519. Found: 488.2517.

Provenance & Evidence