Sodium Sulfite → HCID 86668867, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-methylenecyclopentanecarboxamide (535 mg, 1.197 mmol) and sodium bicarbonate (141 mg, 1.676 mmol) in methylene chloride (4 mL) and water (2 mL) was cooled to 5° C. and treated with m-CPBA (318 mg, 1.436 mmol). The mixture was stirred at 5° C. for 1 hour, then allowed to warm to room temperature and stirred for 18 hours. The mixture was cooled to 5° C., treated with saturated sodium sulfite, and stirred at room temperature for 30 minutes. The layers were separated, and the aqueous phase was extracted 3× with methylene chloride. The organic phases were combined and concentrated in vacuo, and the residue was taken up in ethyl acetate. The solution was washed 3× with saturated sodium carbonate, once with water, and once with brine, then dried over sodium sulfate, and concentrated in vacuo to yield the title compound (535 mg, 1.155 mmol, 97% yield) as a glass and a mixture of diastereomers. 1H NMR (400 MHz, CD3OD) (NMR shows several rotomers) δ ppm 7.54-7.40 (m, 2 H), 7.37-7.26 (m, 2 H), 4.90-4.82 (m, 1 H+H2O), 4.63-4.48 (m, 0.6 H), 4.12-3.96 (m, 1 H+residual ethyl acetate), 3.68-3.46 (m, 1.6 H), 3.23-3.02 (m, 1.6 H), 2.98-2.90 (m, 0.4 H), 2.90-2.77 (m, 2 H), 2.76-2.53 (m, 1 H), 2.31-1.79 (m, 6 H+residual ethyl acetate), 1.79-1.64 (m, 1.6 H), 1.60 (bd, 0.4 H, J=14.1 Hz), 1.57-1.48 (m, 0.6 H), 1.04 (dd, 1.4 H, J=6.6, 3.1 Hz), 1.00 (t, 1.6 H, J=6.4 Hz), 0.96-0.90 (m, 3.2 H), 0.87-0.79 (dd, 3 H, J=5.5, 3.0 Hz), 0.79-0.71 (m, 3 H).

Provenance & Evidence