Water → HCID 178523577, compound

Participants

Reaction Steps

To a round bottomed flask was added trans-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]-3-nitrobenzamide (52 mg), dichloroethane (9 ml), water (3 ml), and trifluoroacetic acid (3 ml). The reaction mixture was heated under reflux for 15 hr, cooled to room temperature, and toluene (15 ml) was added. The reaction mixture was concentrated in vacuo, methanol (15 ml) was added, and further concentrated to remove residual trifluoroacetic acid. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, gradient elution using 1:3, then 1:1, v/v) furnished the title compound (20 mg, 63%) as a white solid. δH ((CD3)2CO): 1.52-1.68 (4H, m), 1.87-1.95 (2H, m), 2.09-2.17 (2H, m), 2.87 (1 H, tt), 3.97-4.08 (1 H, m), 6.30 (1 H, dd), 6.38 (1 H, d), 6.99 (1 H, d), 7.77 (1H, t), 7.90 (1H, s), 7.96 (1 H, d), 8.05 (1 H, s), 8.33 (1 H, dd), 8.37 (1 H, dd), 8.68 (1 H, t); m/z (ES+) 357 )M+H)+.

Provenance & Evidence