Potassium Carbonate → (3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

HRID 1029872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029872
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH2:25][N:26]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:27][Si](C)(C)C)CCC.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O.ClCCl>[CH2:32]([N:26]1[CH2:27][CH:11]2[CH:12]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][C:10]2=[O:13])[CH2:25]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 1382802-Cyclohexen-1-one, 4,4-diphenyl-HCID 11097910N-Benzyl-1-butoxy-N-[(trimethylsilyl)methyl]methanamine3×

Produkt 1

HCID 19384608(3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidKatalysator3×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trifluoroacetic acid (5 drops) is added to a solution of 4,4-diphenyl-cyclohex-2-en-1-one (155 g) and N-butoxymethyl-N-trimethylsilylmethyl-benzylamine (202 cc) in dry dichloromethane (1,000 cc) and the reaction mixture is refluxed for 45 minutes. N-Butoxymethyl-N-trimethylsilylmethyl-benzylamine (50 cc) and trifluoroacetic acid (3 drops) are added and the mixture is stirred for a further 45 minutes under reflux before adding further N-butoxymethyl-N-trimethylsilylmethyl-benzylamine (25 cc) and trifluoroacetic acid (3 drops). The reaction mixture is stirred under reflux for 45 minutes and then treated with potassium carbonate (50 g) and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in isopropyl ether (200 cc) and the solution is cooled at 0° C. for 1 hour. The crystals are drained, washed with isopropyl ether (2 * 15 cc) and dried to give (3aRS,7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone (193 g) in the form of white crystals melting at 132° C.

Aufarbeitung

  1. temperaturethe reaction mixture is refluxed for 45 minutes
  2. temperatureunder reflux
  3. stirringThe reaction mixture is stirred
  4. temperatureunder reflux for 45 minutes
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. dissolutionThe residue is dissolved in isopropyl ether (200 cc)
  8. washwashed with isopropyl ether (2 * 15 cc)
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2acc79e71046423b9514dfbdd1caba4e
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

Notizen zur Reaktion

Wird geladen…