Formic Acid → 2-Cyclopentylethyl sulfamate

Temperature

0 °C

To chlorosulfonyl isocyanate (275 mL, 3.15 mol) at 0° C. was added formic acid (119 mL, 3.15 mol), dropwise. The resulting solid was allowed to stir at 0° C. for a further 20 minutes. The residue was diluted with dichloromethane (875 mL) and warmed to room temperature for one hour. The reaction mixture was cooled in an ice/salt bath and a solution of 2-cyclopentyl ethanol (240 g, 2.1 mol) in pyridine (255 mL, 3.15 mol) and dichloromethane (2.1 L) was added, keeping the temperature below 7° C. After 2 hours, the reaction was concentrated in vacuo, diluted with ethyl acetate, washed with saturated sodium bicarbonate solution and brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a colourless oil. The residue was purified by column chromatography on silica gel, eluting with 90:10 to 50:50 heptane:ethyl acetate, to afford the title compound as a colourless oil in 95% yield (276 g).

1. temperaturewarmed to room temperature for one hour
2. temperatureThe reaction mixture was cooled in an ice/salt bath
3. customthe temperature below 7° C
4. waitAfter 2 hours
5. concentrationthe reaction was concentrated in vacuo
6. additiondiluted with ethyl acetate
7. washwashed with saturated sodium bicarbonate solution and brine
8. dry with materialThe organic layer was dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give a colourless oil
12. customThe residue was purified by column chromatography on silica gel
13. washeluting with 90:10 to 50:50 heptane

ORD record

ord-787e9cc5322b4000a92b4aca18070688

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486992B2