Sodium Hydroxide → 3-[7-(1,3-Dimethyl-1H-pyrazol-5-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-1-butanol

HRID 1674496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674496
[CH3:1][N:2]1[C:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:18])=[N:3]1.[OH:19][CH2:20][CH2:21][C:22](=O)[CH3:23].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][N:13]([CH:22]([CH3:23])[CH2:21][CH2:20][OH:19])[CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:18])=[N:3]1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 1115094-Hydroxy-2-ButanoneHCID 5049666Sodium triacetoxyborohydrideHCID 251050497-(1,3-Dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine2×

Produkt 1

HCID 598642713-[7-(1,3-Dimethyl-1H-pyrazol-5-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-1-butanolAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (0.5 g) (intermediate 3) in tetrahydrofuran (5 ml), at room temperature, 4-hydroxy-2-butanone (0.22 g), glacial acetic acid (0.12 ml) and sodium triacetoxyborohydride (0.53 g) were subsequently added. After stirring over night the mixture was made alkaline with 1N aqueous sodium hydroxide and extracted with dichloromethane. The organic phase was dried with sodium sulphate and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel with 70% cyclohexane-ethyl acetate to give the title compound (0.25 g) as a white solid.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried with sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel with 70% cyclohexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a6a99e3523224e038cfb9e8940c747d5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003638B2

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