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

HRID 30298

Reaktionsgleichung

Reaktionsgleichung von HRID 30298
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b4408763ec0e4384b88052e8aaac8636
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423056B2

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