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

HRID 658263노트

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HRID 658263 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-10 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b56a52258cbb4ffdafa6d1092a6dc506
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076359B2

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