HCID 57565075, compound → HCID 57565073, compound

Participants

Reaction Steps

To a solution of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylcycloheptanol (26 mg, step F) in dichloromethane (0.5 mL) at room temperature were added pyridinium chlorochromate (25 mg) and powdered 4A° molecular sieves (26 mg), and the resulting mixture was stirred at room temperature for 1.5 h and then filtered through a small pad of silica gel. The filtrate was evaporated in vacuo and the residue was purified by preparative TLC eluting with 30% ethyl acetate/70% hexanes to give the title compound as an oily material (21 mg). 1H NMR (400 MHz, CDCl3) δ 1.74 (3H, m), 1.98 (1H, dd, J=11.6, 1.2 Hz), 2.48 (6H, m), 3.37 (1H, d, J=8.8 Hz), 3.39 (1H, d, J=8.8 Hz), 4.42 (2H, s), 7.28 (1H, m), 7.35 (4H, m), 7.56 (2H, m), and 7.74 (1H, s). HRMS m/z calcd. for C23H21F6O2 (M−H)− 443.1446, found 443.1457.

Provenance & Evidence