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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1623902Generated: October 29, 2026

Triethylamine → (R)-2-(tert-Butyldimethylsilyloxy)-1-(pyridin-4-yl)ethyl Methanesulfonate

https://huagongshe.com/reaction/1623902

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantMethanesulfonyl chlorideHCID 31297—
Reactant(R)-2-(tert-butyldimethylsilyloxy)-1-(pyridin-4-yl)ethanolHCID 68182607—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDichloromethaneHCID 6344—
Product(R)-2-(tert-Butyldimethylsilyloxy)-1-(pyridin-4-yl)ethyl MethanesulfonateHCID 86669654—

Reaction Conditions

Temperature0 °C

Reaction Steps

To a stirred solution of (R)-2-(tert-butyldimethylsilyloxy)-1-(pyridin-4-yl)ethanol (80 mg, 0.316 mmol), triethylamine (97 μL, 0.695 mmol) and 4-(dimethylamino)pyridine (3.85 mg, 0.032 mmol) in DCM was added methanesulfonyl chloride (36.8 μL, 0.474 mmol) at 0° C. The reaction was stirred at 0° C. for 20 min, then at room temperature overnight. The mixture was washed with a NaHCO3 solution, water and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to give the title compound without further purification. LCMS m/z=332.3 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778950B2
Source datasetuspto-grants-2014_07
ORD IDord-8266f9c2f58f4f36b31bf4e506099de5
Source noteuspto-grants-2014_07