Sodium Sulfite → Tert-butyl 6-(4-chlorophenyl)-1-methyl-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Temperature

0 °C

A solution of tert-butyl 4-(4-chlorophenyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate (1.09 g, 3.54 mmol) in methylene chloride (15 mL) was cooled to 0° C. and treated dropwise with a solution of m-CPBA (1.111 g, 4.96 mmol) in methylene chloride (15 mL). The reaction was stirred at 0° C. for 1 hour, then allowed to slowly warm to room temperature and stirred overnight. The mixture was cooled to 0° C., treated with saturated aqueous sodium sulfite (20 mL), and stirred for 1 hour. The layers were separated, and the organic phase was washed once with water, 3× with saturated sodium carbonate, once with water, and once with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified over a 120 g silica gel column, eluting at 85 mL/min with a 0% to 17% ethyl acetate/hexanes gradient followed by 17% ethyl acetate/hexanes to yield the title compound as a colorless oil. MS (ESI+)=268.2 (M−tert-Bu)+, 250.1 (M−tert-BuO)+.

1. temperatureto slowly warm to room temperature
2. stirringstirred overnight
3. temperatureThe mixture was cooled to 0° C.
4. stirringstirred for 1 hour
5. customThe layers were separated
6. washthe organic phase was washed once with water, 3× with saturated sodium carbonate, once with water
7. dry with materialonce with brine, dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customThe residue was purified over a 120 g silica gel column
10. washeluting at 85 mL/min with a 0% to 17% ethyl acetate/hexanes gradient

ORD record

ord-9061af68625f4a5e899c30099bca30d8

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501782B2