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

HRID 2041317

反応式

HRID 2041317 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-3b3589badff448a4b935f28242353b8d
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

関連ノート

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