Ethanol → 2-benzyloxy-7,8,9,10-tetrahydro-10-oxo-11-phenyl-6H-9-azepino[1,2-a]indole carboxylic acid ethylester

HRID 66826Notes

Reaction equation

HRID 66826 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:16]=2)[C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:10]1[C:32]([O:34]CC)=O)[CH3:2].C(O)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][CH2:7][CH2:8][N:9]2[C:17]3[C:12]([C:11]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[C:10]2[C:32]1=[O:34])=[CH:13][C:14]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:15][CH:16]=3)=[O:37])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 542507335-(2-ethoxycarbonyl-5-benzyloxy-3-phenyl-1H-indole-1-yl)-valeric acid ethylester

Product 1

HCID 538189352-benzyloxy-7,8,9,10-tetrahydro-10-oxo-11-phenyl-6H-9-azepino[1,2-a]indole carboxylic acid ethylester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Twenty-three grams (46 m mole) of 5-(2-ethoxycarbonyl-5-benzyloxy-3-phenyl-1H-indole-1-yl)-valeric acid ethylester were dissolved in 150 ml of toluene and added dropwise within four hours to a boiling suspension of 5.2 g (46 m mole) of potassium-tert.-butylate in 150 ml of toluene. Then the ethanol formed was distilled off with toluene. After cooling, ice-cold dilute hydrochloric acid was added and the mixture was extracted with toluene. The toluene extracts were evaporated, and the residue was purified by chromatography on silicagel (solvent: toluene).

Workup

  1. distillationwas distilled off with toluene
  2. temperatureAfter cooling
  3. additionice-cold dilute hydrochloric acid was added
  4. extractionthe mixture was extracted with toluene
  5. customThe toluene extracts were evaporated
  6. customthe residue was purified by chromatography on silicagel (solvent: toluene)

Sources & evidence

ORD record
ord-aefba39ab15f4df99be4d825d21ac108
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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