Dimethyl Sulfoxide → HCID 12292874, compound

To a chilled (−70° C.) solution of oxalyl chloride (20 mL, 0.23 mol) in dichloromethane (500 mL) was added dropwise a solution of anhydrous dimethylsulfoxide (34 mL, 0.48 mol) in dichloromethane (50 mL) and the resulting mixture was stirred for 5 min. at a temperature below −60° C. Then a solution of (1R,2R)/(1S,2S)-2-(4-morpholinyl)cyclohexanol (37.05 g, 0.2 mol) in dichloromethane (50 mL) was added dropwise in order to maintain the reaction temperature below −60° C. and the reaction mixture was stirred for 15 min. Triethylamine (140 mL) was added dropwise to the reaction mixture, keeping the reaction temperature below −50° C., and then the reaction mixture was allowed to warm up to room temperature. The reaction mixture was poured into water (600 mL) and the aqueous layer was separated and extracted with dichloromethane (2×500 mL). The combined organic layers were dried over sodium sulfate and the solvent was removed in vacuo. Vacuum distillation yielded 35.1 g (96% yield) of the title compound.

1. temperatureto maintain the reaction temperature below −60° C.
2. stirringthe reaction mixture was stirred for 15 min
3. customthe reaction temperature below −50° C.
4. customthe aqueous layer was separated
5. extractionextracted with dichloromethane (2×500 mL)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. customthe solvent was removed in vacuo
8. distillationVacuum distillation

ORD record

ord-708f9ef1d6e1400581e1003c9e347813

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008342B2