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Dichloromethane → methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-[2,2-dimethyl-3-(t-butyldimethylsilyloxy)propyl]-7H-pyrrolo(2,3-d)carbazole-6-carboxylate

HRID 1905075
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Reaktionsgleichung

Reaktionsgleichung von HRID 1905075
[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[CH:5]([C:15]([O:17][CH3:18])=[O:16])[CH2:4][NH:3][CH2:2]1.[CH3:19][C:20]([CH3:34])([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:21][CH2:22][CH:23]=O.N1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=[CH:36]1.[CH2:42](Cl)Cl>>[CH2:36]([N:3]1[CH:23]2[CH:22]([CH2:21][C:20]([CH3:34])([CH3:19])[CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:4][C:5]([C:15]([O:17][CH3:18])=[O:16])=[C:6]3[NH:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:14]23[CH2:1][CH2:2]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
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Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 64514761H-AzepineHCID 11021133Methyl 1,2,3,4,5,6-hexahydroazepino(4,5-b)indole-5-carboxylateHCID 147501124,4-Dimethyl-5-t-butyldimethylsilyloxyvaleraldehyde

Produkt 1

HCID 14750128methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-[2,2-dimethyl-3-(t-butyldimethylsilyloxy)propyl]-7H-pyrrolo(2,3-d)carbazole-6-carboxylate

Versuchsvorschrift

To a solution of 3.5 g (14.3 mmol) of methyl 1,2,3,4,5,6-hexahydroazepino(4,5-b)indole-5-carboxylate in 175 mL of dry CH2Cl2 at 20° C. was added dropwise, over 2 min., 3.5 g (14.3 mmol, 1 eq) of 4,4-dimethyl-5-t-butyldimethylsilyloxyvaleraldehyde in 25 mL of dry CH2Cl2Stirring was continued overnight (16 h) at 20° C. The solvent was removed under vacuum (aspirator) and the residue taken up in CHCl3 (150 mL). To this yellow solution was added 2.5 mL of benzyl bromide and the mixture heated at reflux for 18 h. The solvent was removed under vacuum (aspirator) and the residue triturated with pentane to give a gummy solid. The pentane was removed by pipette and the gum triturated twice more with additional pentane. To this residue was added 100 mL of dry methanol and 6 mL 4 eq; 0.043 mol) of dry triethylamine and the whole heated at reflux for 3 h. After cooling, the solvent was removed under vacuum (aspirator) and the residue taken up in CH2Cl2 and washed with 10% NazCO3. After drying over MgSO4 and concentration under vacuum (aspirator), the residue was adsorbed on silica gel (20 g) and applied to the top of a silica gel column (200 g, as a slurry in ethyl ether/pentane 3:7). Elution with the latter solvent mixture afforded 5.6 g (70% overall based on the azepine) of the title compound. TLC: (Silica) Rf 0.60 (ethyl ether), detection, CAS, dark blue green with yellow center.

Aufarbeitung

  1. custom(16 h)
  2. customat 20° C
  3. customThe solvent was removed under vacuum (aspirator)
  4. additionTo this yellow solution was added 2.5 mL of benzyl bromide
  5. temperaturethe mixture heated
  6. temperatureat reflux for 18 h
  7. customThe solvent was removed under vacuum (aspirator)
  8. customthe residue triturated with pentane
  9. customto give a gummy solid
  10. customThe pentane was removed by pipette
  11. customthe gum triturated twice more with additional pentane
  12. additionTo this residue was added 100 mL of dry methanol and 6 mL 4 eq
  13. temperature0.043 mol) of dry triethylamine and the whole heated
  14. temperatureat reflux for 3 h
  15. temperatureAfter cooling
  16. customthe solvent was removed under vacuum (aspirator)
  17. washwashed with 10% NazCO3
  18. dry with materialAfter drying over MgSO4 and concentration under vacuum (aspirator)
  19. washElution with the latter solvent mixture
  20. customafforded 5.6 g (70%

Quellen und Nachweise

ORD-Eintrag
ord-fa86e4808eae4919bff06a53b494c1b1
Quelldatensatz
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04841045

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