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

HRID 1623902Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:25][S:26]([O:11][C@H:10]([C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:28])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

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]+.

Workup

customat room temperature
customovernight
washThe mixture was washed with a NaHCO3 solution, water
dry with materialdried over anhydrous Na2SO4
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-8266f9c2f58f4f36b31bf4e506099de5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778950B2

Reaction notes

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