Trifluoroacetic acid → HCID 67915874, compound

HRID 1196237Notes

Reaction equation

HRID 1196237 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-(trimethylsilylmethyl)benzylamine (123 cc) in dry dichloromethane (1000 cc). The reaction mixture is brought to reflux, then stirred for 2 hours while allowing the temperature to return to 25° C. and for a further 15 minutes after the addition of potassium carbonate (60 g). After filtration and concentration to dryness under reduced pressure (2.7 kPa), the crystallized residue is stirred vigorously with isopropyl ether, drained, washed and recrystallized in 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)perhydro-4-isoindolone (92 g) in the form of white crystals. M.p. 124° C.

Workup

  1. temperatureto reflux
  2. waitto return to 25° C. and for a further 15 minutes
  3. filtrationAfter filtration and concentration to dryness under reduced pressure (2.7 kPa)
  4. stirringthe crystallized residue is stirred vigorously with isopropyl ether
  5. washwashed
  6. customrecrystallized in cyclohexane (300 cc)
  7. washwashed with cyclohexane (2×15 cc)
  8. customdried

Sources & evidence

ORD record
ord-378122067a414177ada82c0242fa5b17
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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