Pyridine → (R)-2-Hydroxy-2-(6-methoxypyridin-3-yl)ethyl 4-methylbenzenesulfonate

HRID 657737Notes

Reaction equation

HRID 657737 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C@@H:9]([OH:12])[CH2:10][OH:11])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:11][CH2:10][C@H:9]([OH:12])[C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 58103595(R)-1-(6-methoxypyridin-3-yl)ethane-1,2-diol

Product 1

HCID 58103580(R)-2-Hydroxy-2-(6-methoxypyridin-3-yl)ethyl 4-methylbenzenesulfonateYield 116%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (R)-1-(6-methoxypyridin-3-yl)ethane-1,2-diol (2.7 g, 0.016 mol) and pyridine (10 mL) in CH2Cl2 (100 mL) at 0° C. was added p-toluenesulfonyl chloride (3.6 g, 0.019 mol) in small portions. The mixture was slowly warmed to rt and stirred for 24 h, and then diluted with CH2Cl2 (100 mL). The organic phase was washed with aq. NaHCO3, brine, dried (Na2SO4), and concentrated to yield a solid (6.0 g). LC-MS: 324.0 [M+H]+.

Workup

  1. washThe organic phase was washed with aq. NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-653522023edb4326acf3a1384140cfed
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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