Ethanol → HCID 11547594, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclopentanone (5 mg) in THF (0.10 mL) at room temperature was added piperidine (50 μL) followed by titanium(IV) isopropoxide and the resulting solution was heated at 65° C. in a sealed vial for 2 h. The solution was cooled to room temperature, 100 μL ethanol was added followed by sodium borohydride (4 mg), and the resulting suspension was stirred at room temperature for 1 h. The reaction mixture was then passed through a clean-up extraction column (2 g) and washed with methanol (0.3 mL). The filtrate was evaporated in vacuo, and the residue was purified by preparative TLC eluting with 10% MeOH/1% NH3.H2O/89% CH2Cl2 to give the title compound (1.2 mg). 1H NMR (400 MHz, CDCl3) δ 1.3-2.5 (m), 3.43 (d, J=8.8 Hz), 3.48 (d, J=8.8 Hz), 3.51 (d, J=8.0 Hz), 3.61 (d, J=8.0 Hz), 4.45 (s), 7.1-7.4 (m), 7.53 (s), 7.58 (s), 7.71 (s), and 7.74 (s). HPLC retention time (1.96 min, method A). MS: 486 (MH+).

Provenance & Evidence