Potassium Carbonate → HCID 67915812, compound

HRID 1029951Notes

Reaction equation

HRID 1029951 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:2]=1.C(O[CH2:27][N:28]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:29][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O.ClCCl>[CH2:34]([N:28]1[CH2:29][CH:11]2[CH:12]([C:7]([C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)([C:3]3[CH:2]=[C:1]([CH3:21])[CH:6]=[CH:5][CH:4]=3)[CH2:8][CH2:9][C:10]2=[O:13])[CH2:27]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamineHCID 54188104HCID 54188104, compound

Product 1

HCID 67915812HCID 67915812, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (12 drops) is added to a solution of 4,4-bis-(3-tolyl)cyclohexenone (16.7 g) and N-butoxymethyl-N-trimethylsilylmethylbenzylamine (18.7 cc) in dry dichloromethane (150 cc). The reaction mixture is brought to reflux and then stirred for 3 hours allowing the temperature to return to 25° C. and for a further 10 minutes after addition of potassium carbonate (12 g). After filtering and concentrating the filtrate to dryness under reduced pressure (2.7 kPa), the residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 5 cm, height 50 cm), eluting under a nitrogen pressure of 0.7 bar with a mixture of cyclohexane and ethyl acetate (85/15 by volume) and collecting 25 cc fractions. Fractions 14 to 30 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-2-benzyl-7,7-bis-(3-tolyl)-4-perhydroisoindolone (13.9 g) in the form of white crystals.

Workup

  1. temperatureto reflux
  2. waitto return to 25° C. and for a further 10 minutes
  3. filtrationAfter filtering
  4. concentrationconcentrating the filtrate to dryness under reduced pressure (2.7 kPa)
  5. customthe residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 5 cm, height 50 cm)
  6. washeluting under a nitrogen pressure of 0.7 bar
  7. additionwith a mixture of cyclohexane and ethyl acetate (85/15 by volume)
  8. customcollecting 25 cc fractions
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-c52da505858a49e39027c5ee44ed9752
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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