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

HRID 1721193Notes

Reaction equation

HRID 1721193 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

5 drops of trifluoroacetic acid are added to a solution of 155 g of 4,4-diphenyl-2-cyclohexen-1-one and 202 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine in 1000 cm3 of dry dichloromethane and the reaction mixture is refluxed for 45 minutes. 50 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine and 3 drops of trifluoroacetic acid are added and the mixture is further stirred for 45 minutes under reflux before again adding 25 cm3 of N-butoxymethyl-N-trimethylsilylmethylbenzylamine and 3 drops of trifluoroacetic acid. The reaction mixture is stirred under reflux for 45 minutes and then treated with 50 g of potassium carbonate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in 200 cm3 of isopropyl oxide and the solution is cooled to 0° C. for 1 hour. The crystals are drained, washed twice with 15 cm3 of isopropyl oxide and dried to give 193 g of (3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone in the form of white crystals; melting point 132° C.

Workup

  1. temperaturethe reaction mixture is refluxed for 45 minutes
  2. temperatureunder reflux
  3. stirringThe reaction mixture is stirred
  4. temperatureunder reflux for 45 minutes
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. dissolutionThe residue is dissolved in 200 cm3 of isopropyl oxide
  8. washwashed twice with 15 cm3 of isopropyl oxide
  9. customdried

Sources & evidence

ORD record
ord-0dbb35519ebf46fc994d5dc77a851db3
Source dataset
uspto-grants-1996_04
Patent number
US05508433

Reaction notes

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