Triethylamine → (R)-Methanesulfonic acid 1-(6-methyl-pyridin-2-yl)-ethyl ester

HRID 2041317Notes

Reaction equation

HRID 2041317 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C@H:8]([OH:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([C@H:8]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 45079484(R)-1-(6-methylpyridin-2-yl)ethanol

Product 1

HCID 57656393(R)-Methanesulfonic acid 1-(6-methyl-pyridin-2-yl)-ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (R)-1-(6-methyl-pyridin-2-yl)-ethanol (175 mg, 1.28 mmol) and triethylamine (355 μl, 2.56 mmol) in DCM (5 mL) at 0° C. add methanesulfonyl chloride (148 μl, 1.92 mmol). Stir at 0° C. for 30 min and quench the reaction mixture with saturated aqueous NaHCO3 at the same temperature. Extract the mixture three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (8:2) to give the title compound as a colorless oil (274 mg, 100%).

Workup

  1. customquench the reaction mixture with saturated aqueous NaHCO3 at the same temperature
  2. extractionExtract the mixture three times with EtOAc
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (8:2)

Sources & evidence

ORD record
ord-3b3589badff448a4b935f28242353b8d
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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