Ammonium Chloride → HCID 67714472, Verbindung

HRID 55411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 55411
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.C([O:14][CH:15]1[CH2:23][C:22]([CH3:25])([CH3:24])[CH:21]2[CH:17]([CH2:18][N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:20]2)[C:16]1=[O:33])(=O)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH2:26]([N:19]1[CH2:18][CH:17]2[CH:21]([C:22]([CH3:25])([CH3:24])[CH2:23][CH:15]([OH:14])[C:16]2([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[OH:33])[CH2:20]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 67714110(3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindoloneHCID 178489560HCID 178489560, Verbindung

Produkt 1

HCID 67714472HCID 67714472, VerbindungAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 33.8 g of 2-methoxyphenylmagnesium bromide in 75 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 6.6 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindolone in 75 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution and taken up in 200 cm3 of ethyl ether and 100 g of ice. The organic phase is extracted with 3 times 100 cm3 of ethyl ether, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 500 cm3 of petroleum ether. 2.8 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-dimethyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 190° C.

Aufarbeitung

  1. additionis added dropwise, at room temperature
  2. stirringThe reaction mixture is stirred at room temperature for 15 hours
  3. extractionThe organic phase is extracted with 3 times 100 cm3 of ethyl ether
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallized in 500 cm3 of petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-475038bb2b8a4fef9342ac505496ca28
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624950

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