Potassium Carbonate → HCID 67915832, compound

HRID 1029945Notes

Reaction equation

HRID 1029945 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=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:10]2[CH:9]([C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:13][CH2:12][C:11]2=[O:14])[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 54012949HCID 54012949, compound

Product 1

HCID 67915832HCID 67915832, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 drops) is added to a solution of 4,4-bis-(3-chlorophenyl)-cyclohexenone (26.8 g) and N-butoxymethyl-N-trimethylsilylmethylbenzylamine (33 cc) in dry dichloromethane (200 cc). The reaction mixture is brought to reflux and then stirred for 16 hours after having allowed the temperature to return to 25° C. and for a further 15 minutes after addition of potassium carbonate (16 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 7 cm, height 40 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (75/25 by volume) and collecting 500 cc fractions. Fractions 12 to 18 are combined and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-2-benzyl-7,7-bis-(3-chlorophenyl)-4-perhydroisoindolone (16.2 g) in the form of a yellow oil.

Workup

  1. temperatureto reflux
  2. waitto return to 25° C. and for a further 15 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 7 cm, height 40 cm)
  6. washeluting under a nitrogen pressure of 0.5 bar
  7. additionwith a mixture of cyclohexane and ethyl acetate (75/25 by volume)
  8. customcollecting 500 cc fractions
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-a14a49fbc9b847c8b5e7d72c17c6edef
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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