Dimethylformamide → 3-Tert-butyloxycarbonyl-6-(3-chloropropyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1071044

Reaktionsgleichung

Reaktionsgleichung von HRID 1071044
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:23][CH2:22][C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:14][C:13]=2[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].CN(C=O)C.Br[CH2:30][CH2:31][CH2:32][Cl:33]>CCOC(C)=O>[C:3]([O:7][C:8]([N:10]1[CH2:23][CH2:22][C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]([CH2:30][CH2:31][CH2:32][Cl:33])[C:13]=2[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 22396759tert-butyl 1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

Produkt 1

HCID 223966303-Tert-butyloxycarbonyl-6-(3-chloropropyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (335 mg, 60%) was added to a solution of 3-tert-butyloxycarbonyl 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (1.99 g) and DMF (21.0 mL) at 0° C. The solution was stirred at 0° C. for 30 min and then 1-bromo-3-chloropropane (0.74 mL) was added. The solution was stirred at 0° C. for 1 h and 16 h at room temperature. The solution was diluted with EtOAc, which was washed with water (3×20 mL). The combined aqueous layers were extracted with EtOAc (2×20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The crude material was purified by chromatography (Biotage, silica gel, 4:1-1:1 hexane:EtOAc) to give 1.38 g of the title compound as an oil: 1H NMR (300 MHz, CDCl3) δ 7.50, 7.10-7.40, 4.28, 3.55-3.82, 3.52, 2.95-3.10, 2.15-2.30, 1.51; MS (ESI) m/z 363 (M+).

Aufarbeitung

  1. stirringThe solution was stirred at 0° C. for 1 h and 16 h at room temperature
  2. washwas washed with water (3×20 mL)
  3. extractionThe combined aqueous layers were extracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by chromatography (Biotage, silica gel, 4:1-1:1 hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-308e0816e1a74a6ebfa8694cdf9ac572
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903090B2

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