Trifluoroacetic acid → Methyl 1-benzyl-4-cyclopropylpyrrolidine-3-carboxylate

HRID 1162723노트

반응식

HRID 1162723 반응식
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][C:19](=[O:25])/[CH:20]=[CH:21]/[CH:22]1[CH2:24][CH2:23]1.C(O)(C(F)(F)F)=O.C1CCCCC1>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[CH3:17][O:18][C:19]([CH:20]1[CH:21]([CH:22]2[CH2:24][CH2:23]2)[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12]1)=[O:25]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 8078CyclohexaneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 145855512-Propenoic acid, 3-cyclopropyl-, methyl ester

생성물 1

HCID 68647670Methyl 1-benzyl-4-cyclopropylpyrrolidine-3-carboxylate수율 32.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매4회HCID 21867204Cyclohexane ethylacetate용매

실험 절차

101.1 To a stirred, cooled (0° C.) solution of 3.18 g N-benzyl-N-(methoxymethyl)trimethyl-silylmethylamine (CAS 93102-05-7) in 30 ml CH2Cl2 under an argon atmosphere was added dropwise a solution of 1.69 g (E)-3-cyclopropyl-acrylic acid methyl ester (CAS 59939-11-6; J. Org. Chem. 1990, 55(10), 3097) in 15 ml CH2Cl2 over a period of 20 min. Then a solution of 0.1 ml TFA in 5 ml CH2Cl2 was added dropwise within 10 min. When addition was complete, the mixture (slowly warming up to room temperature) was stirred overnight. Then, the mixture was diluted with CH2Cl2, washed with sat. aq. NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The crude product was isolated by chromatography (silica gel; (gradient: cyclohexane->cyclohexane/EtOAc 7:3) to give 1.14 g (3RS,4RS)-1-benzyl-4-cyclopropyl-pyrrolidine-3-carboxylic acid methyl ester as light yellow oil. MS 260.3 ([M+H]+)

후처리

  1. additionWhen addition
  2. washwashed with sat. aq. NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was isolated by chromatography (silica gel

출처 및 근거

ORD 기록
ord-d510df7ec5e74d2c98518136a1e9ba86
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820699B2

반응 노트

불러오는 중…