Sodium Hydroxide → 1-[Bis(4-chlorophenyl)methyl]-3-[1-(3,5-difluorophenyl)-2,2-dimethylpropylidene]azetidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 80 mg (0.163 mmol) of 1-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-1-(3,5-difluorophenyl)-2,2-dimethylpropan-1-ol (2) in 1 mL of CH2Cl2, 86 uL (0.653 mmol) of DAST was added and it was stirred for 1 h at −78° C. and overnight at rt. Then another 86 uL (0.653 mmol) of DAST was added again and it was stirred 3 h at 38-45° C. Then to the reaction mixture was added 20 mL of CH2Cl2 and 10 mL of ag NaHCO3. The pH was adjusted to 8-9 with 2N NaOH. The water layer was extracted with CH2Cl2 (3×20 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 1.06 (s, 9R), 3.37 (s, 2H), 4.05 (s, 2H), 4.44 (s, 1H), 6.55 (d, J=8 Hz, 2H), 6.67 (m, 1H), 7.25 (d, J=6.6 Hz, 4H), 7.33 (d, J=7 Hz, 4H); Mass Spectrum: m/e=472 (M+1 35Cl, 35Cl) and 474 (M+1 35Cl, 37Cl).

Provenance & Evidence