Trifluoroacetic acid → HCID 67915874, Verbindung

HRID 1029934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029934
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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 67915874HCID 67915874, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1469b5e7a23d4e4081561e217425932c
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

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