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Sodium Hydroxide → 1h-Indole-7-carboxamide,n-[[4-(1,1-dimethylethyl)phenyl]methyl]-2,3-dihydro-n-(2-phenylethyl)-

HRID 855425
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 855425
[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH2:19][CH2:18]3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 866030681H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amide

Produkt 1

HCID 768468721h-Indole-7-carboxamide,n-[[4-(1,1-dimethylethyl)phenyl]methyl]-2,3-dihydro-n-(2-phenylethyl)-Ausbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 310 mg (0.76 mmol) of 1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amide in 5 ml acetic acid cooled to 0° C. were added in portions 142 mg (2.26 mmol) of sodium cyano borohydride. The reaction mixture was stirred for 2 h at 0° C. and 2N aqueous sodium hydroxide solution was added until the reaction mixture was basic. The reaction mixture was extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated to yield 310 mg (100%) of product as a colorless oil. MS (ISP) 413.5 (M+H)+.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with diethyl ether
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ddc5e73ea79b46359cfbe7aeb657b852
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07259183B2

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