Triethylamine → 1,1-dioxidotetrahydro-2H-thiopyran-4-yl methanesulfonate

Temperature

0 °C

Triethylamine (7.80 mL, 55.9 mmol) was added to a solution of 4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide (3.5 g, 23.3 mmol) in dichloromethane (35.0 mL). The reaction solution was cooled to 0° C. and methanesulfonyl chloride (3.25 ml, 41.9 mmol) was added. After 10 minutes, the reaction solution was warmed to room temperature and stirred for 3 h. The reaction was quenched via the addition of saturated aqueous ammonium chloride solution (15 mL). The organic layer was separated and washed with saturated aqueous sodium bicarbonate solution (15 mL) and brine (15 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford an off-white solid. The solid residue was suspended in ethyl acetate (20 mL) and filtered. The filtered solid was then collected and dried in vacuo affording 1,1-dioxidotetrahydro-2H-thiopyran-4-yl methanesulfonate (5.1 g, 95%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.38-2.56 (m, 4 H) 2.94-3.06 (m, 2 H) 3.10 (s, 3 H) 3.23-3.39 (m, 2 H) 5.03 (tt, J=4.74, 2.49 Hz, 1 H)

1. temperaturethe reaction solution was warmed to room temperature
2. customThe reaction was quenched via the addition of saturated aqueous ammonium chloride solution (15 mL)
3. customThe organic layer was separated
4. washwashed with saturated aqueous sodium bicarbonate solution (15 mL) and brine (15 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto afford an off-white solid
9. filtrationfiltered
10. customThe filtered solid was then collected
11. customdried in vacuo

ORD record

ord-a7f0f6f0b48349e382a58fee4cf1da27

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2