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Ammonium Chloride → methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-[4-(trifluoromethyl)phenyl]-4-phenyloctahydroisoindole-3a-carboxylate

HRID 1955405
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1955405
[Mg].[F:2][C:3]([F:12])([F:11])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[CH2:13]([N:20]1[CH2:28][C:27]2([C:29]([O:31][CH3:32])=[O:30])[CH:22]([C:23](=[O:39])[CH2:24][CH2:25][CH:26]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:13]([N:20]1[CH2:28][C:27]2([C:29]([O:31][CH3:32])=[O:30])[CH:22]([C:23]([OH:39])([C:7]3[CH:8]=[CH:9][C:4]([C:3]([F:12])([F:11])[F:2])=[CH:5][CH:6]=3)[CH2:24][CH2:25][CH:26]2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5462224MagnesiumHCID 11302988methyl(3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate

Produkt 1

HCID 86755051methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-[4-(trifluoromethyl)phenyl]-4-phenyloctahydroisoindole-3a-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

0.8 g of magnesium turnings was added to a solution of 7.2 9 of 4-(trifluoromethyl)bromobenzene in 40 cm3 of dry diethyl ether. The reaction mixture was spontaneously brought to reflux for ten minutes and was then heated at reflux for twenty minutes. The reaction mixture was subsequently cooled and a solution of 5.6 g of methyl (3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate in 40 cm3 of dry diethyl ether was added over fifteen minutes at a temperature in the region of 10° C. The reaction mixture was stirred for ten minutes at a temperature in the region of 10° C. and then poured into 150 cm3 of a saturated aqueous ammonium chloride solution. The aqueous phase was separated by settling and extracted with three times 75 cm3 of diethyl ether. The organic phases were combined, washed successively with three times 75 cm3 of distilled water, dried over magnesium sulphate in the presence of 3S charcoal and concentrated under reduced pressure. After crystallization from 25 cm3 of pentane, 5.2 g of methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-[4-(trifluoromethyl)phenyl]-4-phenyloctahydroisoindole-3a-carboxylate were obtained in the form of a beige solid, the characteristic of which was as follows:

Aufarbeitung

  1. temperatureto reflux for ten minutes
  2. temperaturewas then heated
  3. temperatureat reflux for twenty minutes
  4. temperatureThe reaction mixture was subsequently cooled
  5. customThe aqueous phase was separated
  6. extractionextracted with three times 75 cm3 of diethyl ether
  7. washwashed successively with three times 75 cm3 of distilled water
  8. dry with materialdried over magnesium sulphate in the presence of 3S charcoal
  9. concentrationconcentrated under reduced pressure
  10. customAfter crystallization from 25 cm3 of pentane

Quellen und Nachweise

ORD-Eintrag
ord-2db78c5eec584d02b526ee83fc00bdf3
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06124465

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