Iodoacetamide → tert-butyl 6-(2-amino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

HRID 1370386노트

반응식

HRID 1370386 반응식
[CH2:1]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5][CH2:4][N:3]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:2]1.I[CH2:23][C:24]([NH2:26])=[O:25].[H-].[Na+]>CN(C=O)C>[NH2:26][C:24](=[O:25])[CH2:23][N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]2[CH2:1][CH2:2][N:3]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:4][CH2:5][C:6]1=2

참가 물질

5

반응물 3

HCID 3727IodoacetamideHCID 24758Sodium hydride2회HCID 22396759tert-butyl 1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

생성물 1

HCID 22396556tert-butyl 6-(2-amino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate수율 19.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-Butyl 1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0994 g, 0.347) and iodoacetamide (0.0704 g, 0.381 mmol, 1.10 equiv.) was dissolved in DMF (1 mL) at rt under N2. NaH (0.033 g, 0.825 mmol, 2.38 equiv., 60% dispersion) was added, and the reaction mixture was stirred for 16 h. Additional NaH (0.039 g) was added and the reaction mixture was stirred for 1.5 h. The reaction mixture was poured over ice, and the resulting mixture was extracted with EtOAc. The organic extracts was washed with water and then with brine. The organic extracts was dried over MgSO4, filtered, and concentrated. The crude product (0.124 g) was purified by PTLC (2×1 mm×20 cm×20 cm SiO2 plates, developed with 3:1 EtOAc:hexane, eluted with 10% MeOH in CH2Cl2) to give tert-butyl 6-(2-amino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.0233 g) in 19% yield. 1H NMR (300 MHz, CDCl3) δ 1.50, 2.93-3.07, 3.68-3.79, 4.71, 5.33, 5.90-5.94, 7.15-7.24, 7.50-7.54; MS (ESI+) for C19H25N3O3 m/z 344.1 (M+H)+.

후처리

  1. stirringthe reaction mixture was stirred for 1.5 h
  2. additionThe reaction mixture was poured over ice
  3. extractionthe resulting mixture was extracted with EtOAc
  4. washThe organic extracts was washed with water
  5. dry with materialThe organic extracts was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product (0.124 g) was purified by PTLC (2×1 mm×20 cm×20 cm SiO2 plates, developed with 3:1 EtOAc:hexane, eluted with 10% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-420d6e9c5da14be2b18299105f67e64f
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583135B2

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