2-Benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

HRID 2211411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2211411
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:12][CH:13]([OH:26])[C:14]2([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[OH:17])[CH2:9]1)C1C=CC=CC=1>C(O)C>[C:33]1([C:11]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:10]3[CH:15]([CH2:16][NH:8][CH2:9]3)[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH:13]([OH:26])[CH2:12]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

3

Edukt 1

HCID 193768282-Benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

Produkt 1

HCID 19047650(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediolAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 2 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol and 50 cm3 of ethanol is heated at 65° C., while stirring; 0.65 g of 20% palladium hydroxide-on-charcoal is added and the reaction mixture is then hydrogenated at a temperature of 65° C. and under atmospheric pressure, while stirring. After a reaction time of 1 hour, the theoretical volume of hydrogen has been absorbed; the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallised in 10 cm3 of isopropyl ether. 1.45 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol which melts at 230° C. are obtained.

Aufarbeitung

  1. customis then hydrogenated at a temperature of 65° C. and under atmospheric pressure
  2. stirringwhile stirring
  3. customAfter a reaction time of 1 hour, the theoretical volume of hydrogen has been absorbed
  4. filtrationthe reaction mixture is filtered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallised in 10 cm3 of isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3553e6ed9ff041dcb891bc30f4f7b1ca
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05463077

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