Trifluoroacetic acid → Ethyl 1-benzyl-3-cyanopyrrolidine-3-carboxylate

HRID 1618957

반응식

HRID 1618957 반응식
C(O)(C(F)(F)F)=O.[C:8]([C:10](=[CH2:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9].[CH2:17]([N:24]([CH2:28][Si](C)(C)C)[CH2:25]OC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH2:17]([N:24]1[CH2:25][CH2:16][C:10]([C:8]#[N:9])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:28]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 81530Ethyl cyanoacrylateHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

생성물 1

HCID 67228450Ethyl 1-benzyl-3-cyanopyrrolidine-3-carboxylate수율 94%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

TFA (4.31 mmol, 0.49 g) was added to a solution of ethyl 2-cyanoacrylate (17.58 mmol, 2.20 g) in DCM (100 mL) under nitrogen atmosphere. Subsequently, a solution of N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (21.49 mmol, 5.10 g) in DCM (50 mL) was added dropwise while cooling with an ice-bath in order to keep the reaction temperature at room temperature (exothermic reaction). The reaction mixture was stirred overnight at room temperature. Then the mixture was washed with saturated aqueous NaHCO3 (100 mL). The aqueous phase was extracted with DCM (100 mL). The combined organic phase was dried over MgSO4 and evaporated in vacuo. The crude product was purified by flash silicagel chromatography (100% heptane to 50% EtOAc) yielding 4.27 g of a colorless oil (94%). 1H-NMR (400 MHz, CDCl3, 300K): δ=1.32 (3H, t, J=7.1 Hz), 2.44 (1H, m), 2.59 (1H, m), 2.69 (1H, m), 2.89 (1H, m), 2.99 (1H, d, J=9.8 Hz), 3.17 (1H, d, J=9.8 Hz), 3.69 (2H, s), 4.27 (2H, q, J=7.1 Hz), 7.29 (5H, m).

후처리

  1. temperaturewhile cooling with an ice-bath in order
  2. customat room temperature
  3. custom(exothermic reaction)
  4. washThen the mixture was washed with saturated aqueous NaHCO3 (100 mL)
  5. extractionThe aqueous phase was extracted with DCM (100 mL)
  6. dry with materialThe combined organic phase was dried over MgSO4
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash silicagel chromatography (100% heptane to 50% EtOAc)

출처 및 근거

ORD 기록
ord-e83238cfeb92442da7de8250fe822996
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772286B2

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