Potassium Carbonate → HCID 54361557, compound

HRID 1029931Notes

Reaction equation

HRID 1029931 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=[CH: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:9]2[CH:8]([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)[CH:12]=[CH:11][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 2968354,4-Diphenyl-2,5-cyclohexadien-1-oneHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine2×

Product 1

HCID 54361557HCID 54361557, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 drops) is added to a solution of 4,4-diphenyl-cyclohexa-2,5-dien-1-one (7.7 g) and N-butoxymethyl-N-trimethylsilylmethylbenzylamine (11 cc) in dry dichloromethane (80 cc) and the reaction mixture is refluxed for 1 hour and a half. Additional N-butoxymethyl-N-trimethylsilylmethylbenzylamine (5 cc) and trifluoroacetic acid (2 drops) are added and the reaction mixture is heated for 1 hour and a half. The reaction mixture is treated with potassium carbonate (3 g) and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from isopropyl ether (15 cc). The crystals obtained are drained, washed with isopropyl ether (2×5 cc) and dried; (3aRS,7aRS)-2-benzyl-7,7-diphenyl-2,3,3a,4,7,7a-hexahydro-4-1H-isoindolone (4.4 g) melting at 132° C. is obtained.

Workup

  1. temperaturethe reaction mixture is refluxed for 1 hour
  2. temperaturethe reaction mixture is heated for 1 hour
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is crystallized from isopropyl ether (15 cc)
  6. customThe crystals obtained
  7. washwashed with isopropyl ether (2×5 cc)
  8. customdried

Sources & evidence

ORD record
ord-3db2d645d5e84673811b268d62fc1440
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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