Trifluoroacetic acid → 2-Benzyloctahydro-4H-isoindol-4-one

HRID 30298

반응식

HRID 30298 반응식
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1.C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH:22]2[CH:21]([CH2:20][CH2:19][CH2:18][C:17]2=[O:23])[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 135942-Cyclohexen-1-oneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

생성물 1

HCID 438112032-Benzyloctahydro-4H-isoindol-4-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Benzyl-methoxymethyl-trimethylsilanylmethyl-amine (29.6 g, 0.12 mol) was added to a solution of cyclohex-2-enone (10 g, 0.104 mol) in 500 mL of dichloromethane at 0° C. followed by the dropwise addition of 10 mol % TFA dissolved in 2 mL of dichloromethane. The reaction mixture was stirred at room temperature overnight and was quenched with 50 mL of saturated NaHCO3. The organic layer was washed with 500 mL of brine, dried with MgSO4 and solvent was evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using a 2-45% ethylacetate-hexane gradient to afford the subtitle compound. (13.8 g, 60%). MS calculated for C15H19NO+H: 230, observed: 230.

후처리

  1. customwas quenched with 50 mL of saturated NaHCO3
  2. washThe organic layer was washed with 500 mL of brine
  3. dry with materialdried with MgSO4 and solvent
  4. customwas evaporated in vacuo
  5. customto give the crude product that
  6. customwas purified by column chromatography (SiO2)

출처 및 근거

ORD 기록
ord-b4408763ec0e4384b88052e8aaac8636
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423056B2

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