tert-Butanol → 5-hydroxymethyl-5-hydroxy-1-(4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 745088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745088
[CH2:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1.C(O)(C)(C)C.[OH2:36].[OH2:37].C[N+]([O-])(C)C.S([O-])(O)=O.[Na+]>[Os](=O)(=O)(=O)=O.N1C=CC=CC=1.O>[OH:36][CH2:1][C:2]1([OH:37])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=[O:30])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3]1

Komponenten

8

Edukt 4

HCID 6386tert-ButanolHCID 198430Trimethylamine oxide dihydrateHCID 19608041HCID 19608041, VerbindungHCID 23665763Sodium Bisulfite

Produkt 1

HCID 196079655-hydroxymethyl-5-hydroxy-1-(4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To 5-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.60 g) are added successively t-butyl alcohol (6.0 ml), water (1.2 ml), pyridine (0.3 ml), osmium tetroxide (1.2 mg) and trimethylamine N-oxide dihydrate (0.22 g), and the mixture is refluxed with stirring for 2.5 hours. After cooling, to the reaction solution is added 20% aqueous sodium hydrogensulfite solution (10 ml), and the mixture is stirred at room temperature for 1.5 hour. The reaction solution is extracted with a mixture of ethyl acetate/tetrahydrofuran (1:1). The extract is washed successively with diluted hydrochloric acid and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is recrystallized from ethyl acetate/n-hexane to give 5-hydroxymethyl-5-hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.55 g) as white powder, m.p. 136°-140° C.

Aufarbeitung

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling, to the reaction solution
  3. stirringthe mixture is stirred at room temperature for 1.5 hour
  4. extractionThe reaction solution is extracted with a mixture of ethyl acetate/tetrahydrofuran (1:1)
  5. washThe extract is washed successively with diluted hydrochloric acid and saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is recrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-50042dcff098472eaca76a202396f18e
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559230

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