Trifluoroacetic acid → HCID 67915874, compound

HRID 1029934Notes

Reaction equation

HRID 1029934 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([C:15]2([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[CH:16]2)[CH:12]=[CH:13][CH:14]=1.C(O[CH2:34][N:35]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:36][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:41]([N:35]1[CH2:36][CH:17]2[CH:16]([C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([F:8])[CH:10]=3)[CH2:20][CH2:19][C:18]2=[O:21])[CH2:34]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamineHCID 543073284,4-Bis(3-fluorophenyl)cyclohexenone

Product 1

HCID 67915874HCID 67915874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 cc) is added to a solution of 4,4-bis-(3-fluorophenyl)cyclohexenone (90.3 g) and N-butoxymethyl-N-trimethylsilylmethylbenzylamine (123 cc) in dry dichloromethane (1,000 cc). The reaction mixture is brought to reflux and then stirred for 2 hours allowing the temperature to return to 25° C. and is then stirred for a further 15 minutes after addition of potassium carbonate (60 g). After filtering and concentrating the filtrate to dryness under reduced pressure (2.7 kPa), the crystallized residue is scraped with isopropyl ether, drained, washed and recrystallized from cyclohexane (300 cc). The crystals are drained, washed with cyclohexane (2×15 cc) and dried to give (3aRS,7aRS)-2-benzyl-7,7-bis-(3-fluorophenyl)-4-perhydroisoindolone (92 g) in the form of white crystals. m.p.=124° C.

Workup

  1. temperatureto reflux
  2. customto return to 25° C.
  3. stirringis then stirred for a further 15 minutes
  4. filtrationAfter filtering
  5. concentrationconcentrating the filtrate to dryness under reduced pressure (2.7 kPa)
  6. washwashed
  7. customrecrystallized from cyclohexane (300 cc)
  8. washwashed with cyclohexane (2×15 cc)
  9. customdried

Sources & evidence

ORD record
ord-1469b5e7a23d4e4081561e217425932c
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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