Dimethyl Sulfoxide → HCID 15718161, compound

Temperature

-78 °C

Freshly distilled oxalyl chloride (4.2 ml, 47.3 mmol) was dissolved in 80 ml of methylene chloride and cooled to -78° C. A solution of DMSO (6.7 ml, 94.6 mmol) in 20 ml of methylene chloride was added dropwise to the cooled solution. After stirring 10 minutes, a solution of 3-hydroxymethyl-1-azabicyclo[2.2.2]oct-2-ene (6 g, 43 mmol) in 20 ml of methylene was added dropwise and the reaction stirred for 1 hour. Triethylamine (30 ml, 215 mmol) was added to the reaction and the reaction was slowly warmed to room temperature, then poured into 200 ml of water and the organic phase separated. The aqueous phase was extracted with methylene chloride (3×250 ml) and the combined organic phases were washed with 10% sodium carbonate (2×150 ml), dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a yellow liquid. The crude liquid was stirred in diethyl ether, filtered, and concentrated to afford a clear, yellow liquid (4 g) which was distilled (42° C., 0.25 mm Hg) to give the product as a clear, colorless liquid (2.4 g, 40%).

1. stirringthe reaction stirred for 1 hour
2. temperaturethe reaction was slowly warmed to room temperature
3. customthe organic phase separated
4. extractionThe aqueous phase was extracted with methylene chloride (3×250 ml)
5. washthe combined organic phases were washed with 10% sodium carbonate (2×150 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo
8. customto afford a yellow liquid
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-4ed5c19f4e464edf9dbe265793eb702b

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04937239