Dichloromethane → HCID 11476622, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 47 mg (0.099 mmol) of 1-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-1-(3,5-difluorophenyl)-2-methylpropan-2-ol in 0.5 mL of CH2Cl2 52 uL (0.395 mmol) of DAST (diethylaminosulfur trifluoride) was added and the solution was stirred for 2 h at −78° C. Then to the reaction mixture was added 10 mL of ether and 3 mL of ag NaHCO3. The pH was adjusted to 8-9 with 2N NaOH. The water layer was extracted with CH2Cl2 (3×10 mL). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound as a white solid; 1H NMR (CDCl3) δ 1.51 (s, 3H), 1.71 (s, 3H), 2.60 (t, J=7.8 Hz, 2H), 3.36 (t, J=7.6 Hz, 2H), 3.70 (m, 1H), 4.06 (s, 1H), 6.56 (m, 2H), 6.73 (m, 1H), 7.24 (m, 8H); Mass Spectrum: m/e=458 (M+1 35Cl, 35Cl) and 460 (M+1 35Cl, 37Cl).

Provenance & Evidence