Sodium borohydride → ethyl 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate

HRID 1748265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748265
[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[CH:7]=[C:6]1[C:19]([O:21]CC)=O)#[N:2].[BH4-].[Na+]>C1COCC1.CO.CCOC(C)=O>[O:21]=[C:19]1[C:6]2=[CH:7][C:8]3[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:13]=3[N:5]2[CH2:4][CH2:3][CH2:1][NH:2]1

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydride2×HCID 67235491diethyl 1-(2-cyanoethyl)-1H-indole-2,6-dicarboxylate

Produkt 1

HCID 67235463ethyl 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of diethyl 1-(2-cyanoethyl)-1H-indole-2,6-dicarboxylate (1.5 g, 4.8 mmol) in THF (12 mL) and methanol (16 mL) is added CoCl2 (1.3 g, 9.6 mmol). The bright blue suspension/solution is cooled to 0° C., and NaBH4 (1.8 g, 48.0 mmol) is carefully added in small portions. As each portion is added H2 is formed violently and the suspension becomes black. After the addition of NaBH4 is complete, the mixture is warmed up room temperature for 60 min and is then heated at reflux for 16 h. The mixture is cooled to room temperature and is diluted with EtOAc. The mixture is filtered through Celite, and the gummy solids are washed with EtOAc. The combined EtOAc filtrate is washed with 3M HCl, water, NaHCO3, brine, dried (Na2SO4) and concentrated to afford the title crude compound (1.1 g, 85%) which is used in the next step without purification.

Aufarbeitung

  1. additionAs each portion is added H2
  2. customis formed violently
  3. temperaturethe mixture is warmed up room temperature for 60 min
  4. temperatureis then heated
  5. temperatureat reflux for 16 h
  6. temperatureThe mixture is cooled to room temperature
  7. filtrationThe mixture is filtered through Celite
  8. washthe gummy solids are washed with EtOAc
  9. washThe combined EtOAc filtrate is washed with 3M HCl, water, NaHCO3, brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4fe57b1766ca47019f3a347e9f0c3805
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150577B2

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