Potassium Carbonate → (3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

HRID 1196230Notes

Reaction equation

HRID 1196230 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH2:25][N:26]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:27][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O.ClCCl>[CH2:32]([N:26]1[CH2:27][CH:11]2[CH:12]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][C:10]2=[O:13])[CH2:25]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1382802-Cyclohexen-1-one, 4,4-diphenyl-HCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine3×

Product 1

HCID 19384608(3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalyst3×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (5 drops) is added to a solution of 4,4-diphenyl-2-cyclohexen-1-one (155 g) and N-butoxymethyl-N-(trimethylsilylmethyl)benzylamine (202 cc) in dry dichloromethane (1000 cc), and the reaction mixture is heated to reflux for 45 minutes. N-Butoxymethyl-N-(trimethylsilylmethyl)benzylamine (50 cc) and trifluoroacetic acid (3 drops) are added and the mixture is stirred for a further 45 minutes under reflux before N-butoxymethyl-N-(trimethylsilylmethyl)benzylamine (25 cc) and trifluoroacetic acid (3 drops) are added again. The reaction mixture is stirred under reflux for 45 minutes, then treated with potassium carbonate (50 g), filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in isopropyl ether (200 cc) and the solution cooled to 0° C. for 1 hour. The crystals are drained, washed with isopropyl ether (2×15 cc) and dried to give (3aRS,7aRS)-2-benzyl-7,7-diphenylperhydro-4-isoindolone (193 g) in the form of white crystals, m.p. 132° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 45 minutes
  3. additionare added again
  4. stirringThe reaction mixture is stirred
  5. temperatureunder reflux for 45 minutes
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. dissolutionThe residue is dissolved in isopropyl ether (200 cc)
  9. washwashed with isopropyl ether (2×15 cc)
  10. customdried

Sources & evidence

ORD record
ord-00575f4b58e84908a7823340ce5169e7
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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