Dimethyl Sulfoxide → HCID 11328654, compound

Participants

Reaction Steps

To a solution of 110 uL (1.26 mmol) of oxalyl chloride in 10 mL of methylene chloride was slowly added 180 uL (2.52 mmol) of DMSO at −78° C., followed by stirring for 20 minutes. Then a solution of 292 mg (0.63 mmol) of 1-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-1-(3,5-difluorophenyl)propan-2-ol in 2 mL of methylene chloride was added into the reaction mixture, followed by stirring for 30 minutes at −78° C. Then 435 uL (3.15 mmol) of triethylamine was added at −78° C. and the mixture was stirred for 1 h while it warmed from −78° C. to rt. The mixture was poured into 30 mL of ether and washed with 5 mL of aq NaHCO3. The organic layer was dried over Na2SO4 and concentrated to afford the title compound. NMR (CDCl3) δ 2.09 (s, 3H), 2.65 (m, 1H), 2.78 (m, 1H), 3.08 (m, 2H), 3.45 (m, 1H), 3.90 (d, J=10.5 Hz, 1H), 4.28 (s, 1H), 6.73-6.77 (m, 3H), 7.24-7.33 (m, 8H); Mass Spectrum: m/e=460 (M+1 35Cl, 35Cl) and 462 (M+1 35Cl, 37Cl).

Provenance & Evidence