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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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HRID 855425 반응식
[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]
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5

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ddc5e73ea79b46359cfbe7aeb657b852
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07259183B2

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