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

HRID 911436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911436
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6032a6bb22f94cbebbbcac7c892c9f96
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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