Triethylamine → 1-(Methanesulfonyl)piperidin-3-ol

Temperature

0 °C

Piperidin-3-ol (5.0 g, 49.4 mmol) was dissolved in 1/1 THF/methylene chloride (100 mL). Triethylamine (17 mL, 123 mmol) was added, and the solution was cooled to 0° C. Methanesulfonyl chloride (4.0 mL, 52 mmol) was added dropwise. The mixture was warmed to r.t. and stirred overnight. The reaction was diluted with ethyl acetate (800 mL), washed with 1 N HCl (100 mL), water (75 mL), saturated aqueous sodium bicarbonate (75 mL) and brine (75 mL), and then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and purified via silica gel chromatography (ethyl acetate) to afford the title compound as a clear oil.

1. temperatureThe mixture was warmed to r.t.
2. washwashed with 1 N HCl (100 mL), water (75 mL), saturated aqueous sodium bicarbonate (75 mL) and brine (75 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationThe solvent was concentrated under reduced pressure
5. custompurified via silica gel chromatography (ethyl acetate)

ORD record

ord-e02860db1c6e4a3aad97a78666f101b2

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07186715B2