Water → HCID 86652105, compound

HRID 1845114Notes

Reaction equation

HRID 1845114 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15]([CH:18]([F:20])[F:19])=[CH:16][CH:17]=1)[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:21][S:22](Cl)(=[O:24])=[O:23].CCN(CC)CC.O>C(Cl)Cl>[CH3:21][S:22]([O:11][C@H:10]([C:12]1[CH:13]=[N:14][C:15]([CH:18]([F:20])[F:19])=[CH:16][CH:17]=1)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67053743HCID 67053743, compound

Product 1

HCID 86652105HCID 86652105, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-2-(tert-butyldimethylsilyloxy)-1-(6-(difluoromethyl)pyridin-3-yl)ethanol (3.0 g, 9.90 mmol) in dry CH2Cl2 at 0° C. was added MeSO2Cl (1.2 g, 10.9 mmol) and Et3N (1.3 g, 12.9 mmol). The resulting reaction mixture was warmed to room temperature over a period of 2 h. After completion of the reaction, the reaction mixture was treated with water and extracted with CH2Cl2. The organic layer was dried over anhydrous Na2SO4 and the solvents were evaporated in vacuo. The residue was purified by column chromatography (SiO2, 10% EtOAc/pet. ether) to afford the title compound (2.26 g, 60% yield). MS: 381 [M+1]+; 1H-NMR (300 MHz, CDCl3): 8.67 (s, 1H), 7.90 (d, 1H, J=8.3 Hz), 7.68 (d, 1H, J=8.3 Hz), 6.65 (t, 1H, J=55.2 Hz), 5.62-5.66 (m, 1H), 3.98 (dd, 1H, J=11.2, 6.8 Hz), 3.87 (dd, 1H, J=11.2, 4.9 Hz), 3.028 (s, 3H), 0.87 (s, 9H), 0.04-0.05 (m, 6H).

Workup

  1. customThe resulting reaction mixture
  2. customAfter completion of the reaction
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customthe solvents were evaporated in vacuo
  6. customThe residue was purified by column chromatography (SiO2, 10% EtOAc/pet. ether)

Sources & evidence

ORD record
ord-bf2d6bb45c9b4365942fa9b0e673159b
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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