Trifluoroacetic acid → 1-Benzyl-3-nitro-4-phenylpyrrolidine

HRID 590778

반응식

HRID 590778 반응식
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].C(O)(C(F)(F)F)=O.[CH2:19]([N:26]([CH2:30][Si](C)(C)C)[CH2:27]OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:19]([N:26]1[CH2:30][CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:4]([N+:1]([O-:3])=[O:2])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5284459beta-nitrostyrene, (E)-

생성물 1

HCID 580091801-Benzyl-3-nitro-4-phenylpyrrolidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (E)-(2-nitrovinyl)benzene (110 g, 0.738 mol) and TFA (8.42 g, 0.073 mol) in DCM (500 mL) was added N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)-methanamine (351.4 g, 1.476 mol) in DCM (500 mL) drop-wise at 0° C. for a period of 30 min. Then the reaction mixture was stirred at room temperature for 48 h. After completion of the reaction, the mixture was concentrated in vacuo, dissolved in water, and extracted into EtOAc (×2, 1.0 L). The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified via flash chromatography (20-80% petroleum ether/EtOAc) to afford (3S and R, 4R and S)-1-benzyl-3-nitro-4-phenylpyrrolidine. MS ESI calc'd. For C17H18N2O2 [M+1]+ 283. found 283.

후처리

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutiondissolved in water
  4. extractionextracted into EtOAc (×2, 1.0 L)
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash chromatography (20-80% petroleum ether/EtOAc)

출처 및 근거

ORD 기록
ord-61ee15ffb2a74b249eb2cacf9d013f34
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233979B2

연결된 노트

불러오는 중…