Triethylamine → (1-(Cyanomethyl)cyclopropyl)methyl Methanesulfonate

HRID 658263ノート

反応式

HRID 658263 の反応式
[OH:1][CH2:2][C:3]1([CH2:6][C:7]#[N:8])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:1][CH2:2][C:3]1([CH2:6][C:7]#[N:8])[CH2:5][CH2:4]1)(=[O:19])=[O:18]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 99640761-(Hydroxymethyl)cyclopropaneacetonitrile

生成物 1

HCID 18353775(1-(Cyanomethyl)cyclopropyl)methyl Methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-10 °C

実験手順

To a solution of [1-(hydroxymethyl)cyclopropyl]acetonitrile (prepared according to the procedure described in WO2005/105749 Example 2/Step 4, incorporated by reference) (1 eq.) in DCM at −40° C. was added triethylamine (3 eq.) and then methanesulfonyl chloride (1.5 eq.). The reaction was warmed to −10° C. over 1 h, and it was diluted with DCM and quenched with saturated aqueous NaHCO3. The aqueous phase was extracted with DCM. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 0%→50% EtOAc in Hex) to afford the title compound as an oil.

後処理

  1. customat −40° C.
  2. customquenched with saturated aqueous NaHCO3
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (SiO2, 0%→50% EtOAc in Hex)

出典と根拠

ORDレコード
ord-b56a52258cbb4ffdafa6d1092a6dc506
出典データセット
uspto-grants-2011_12
特許番号
US08076359B2

反応ノート

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