Sodium Carbonate → (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydro-4-isoindolone

HRID 375445Notes

Reaction equation

HRID 375445 reaction equation
[C:1]([O:4][CH:5]1[C:10](=[O:11])[CH:9]=[CH:8][C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)(=[O:3])[CH3:2].C(O[CH2:29][N:30]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:31][Si](C)(C)C)CCC.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O.ClCCl>[C:1]([O:4][CH:5]1[CH2:6][C:7]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]2[CH:9]([CH2:29][N:30]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:31]2)[C:10]1=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamineHCID 151837846-Acetoxy-4,4-diphenyl-2-cyclohexenone

Product 1

HCID 15183785(3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydro-4-isoindolone

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

15 drops of trifluoroacetic acid are added to a solution of 86 g of 6-acetoxy-4,4-diphenyl-2-cyclohexenone and 96 cm3 of N-butoxymethyl-N(trimethylsilylmethyl)benzylamine in 1000 cm3 of dichloromethane. The reaction mixture is stirred at room temperature for 15 hours, 2 g of sodium carbonate are then added and the mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 7 cm, height 70 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (20/80 by volume) and collecting fractions of 200 cm3. Fractions 6 to 10 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 70 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydroisoindol-4-one are obtained in the form of a honey (melting point below 40° C.).

Workup

  1. concentrationthe mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customThe residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 7 cm, height 70 cm)
  3. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (20/80 by volume)
  4. customcollecting fractions of 200 cm3
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-95d52a9a58844a01be06a848760d7e91
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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