Triethylamine → (3aRS,7aRS)-2-[(4-fluorophenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone

HRID 1029875

Reaktionsgleichung

Reaktionsgleichung von HRID 1029875
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[C:13]1([C:19]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:27]3[CH:23]([CH2:24][NH:25][CH2:26]3)[C:22](=[O:28])[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:25]2[CH2:24][CH:23]3[CH:27]([C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:20][CH2:21][C:22]3=[O:28])[CH2:26]2)=[O:11])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Produkt 1

HCID 67916015(3aRS,7aRS)-2-[(4-fluorophenyl)acetyl]-7,7-diphenyl-4-perhydroisoindoloneAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N,N'-Carbonyldiimidazole (1.13 g) is added to a solution of 2-(4-fluorophenyl)acetic acid (1.08 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 1 hour at +5° C. and a solution of 7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.3 g) and triethylamine (0.98 cc) in dichloromethane (40 cc) is then added. The reaction mixture is stirred for 1 hour at +5° C. and then for 16 hours at 20° C. The reaction mixture is washed with distilled water (3×50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized form acetonitrile (5 cc). The crystals are drained, washed with isopropyl ether (10 cc) and dried. (3aRS,7aRS)-2-[(4-fluorophenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (2 g) melting at 210° C. is obtained.

Aufarbeitung

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred for 1 hour at +5° C.
  3. waitfor 16 hours at 20° C
  4. washThe reaction mixture is washed with distilled water (3×50 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe residue is recrystallized form acetonitrile (5 cc)
  9. washwashed with isopropyl ether (10 cc)
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ff99ab3310074621bc8fc730482aea9a
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

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