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

HRID 2041317

반응식

HRID 2041317 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3b3589badff448a4b935f28242353b8d
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580780B2

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