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

HRID 30298

Reaction equation

HRID 30298 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b4408763ec0e4384b88052e8aaac8636
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Linked notes

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