Methanesulfonyl chloride → HCID 12012457, compound

HRID 1804611Notes

Reaction equation

HRID 1804611 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]([OH:9])[CH3:8].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:10][S:11]([O:9][C@@H:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH3:8])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 642847(1R)-1-(Pyridin-2-yl)ethan-1-ol

Product 1

HCID 12012457HCID 12012457, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.27 g (2.2 mmol) of commercially available (1R)-1-pyridin-2-ylethanol in 5 mL of anhydrous dichloromethane was added 0.53 g (4.3 mmol) of 4-(dimethylamino)pyridine followed by 0.20 mL (2.6 mmol) of methanesulfonyl chloride. The resulting mixture was stirred with gradual warming to ambient temperature over 1 h. The resulting mixture was quenched with water and extracted with dichloromethane. The combined organics were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness to afford the title compound as a yellow oil (0.35 g, 81% yield).

Workup

  1. customThe resulting mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c80bb55676274e7f81d8c479695944a7
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

Loading…