Dimethylformamide → 2-t-Butoxycarbonyl-9-(2-acetoxy-ethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 2301088Notes

Reaction equation

HRID 2301088 reaction equation
CN(C=O)C.[C:6]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].[C:28]([O:31][CH2:32][CH2:33]Br)(=[O:30])[CH3:29]>C(OCC)(=O)C>[C:6]([O:10][C:11]([N:13]1[CH2:25][CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:33][CH2:32][O:31][C:28](=[O:30])[CH3:29])[C:15]=2[CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Product 1

HCID 183773002-t-Butoxycarbonyl-9-(2-acetoxy-ethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Anhydrous DMF solution (10 ml) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (2.72 g, 10 mol) was mixed with 60% sodium hydride (0.4 g, 10 mmol) and stirred at room temperature for 1 hour. The reaction solution was cooled to −60° C., mixed with 2-acetoxy-1-bromoethane (1.67 g, 10 mmol) and then returned to room temperature while stirring for 1 hour. The reaction solution was mixed with ethyl acetate, washed with water and dried with anhydrous sodium sulfate, and then the solvent was removed by evaporation under a reduced pressure, the thus obtained residue was mixed with diisopropyl ether (20 ml) and the thus precipitated crystals were collected by filtration to obtain 1.90 g of the title compound (5.3 mmol, 53% in yield).

Workup

  1. temperatureThe reaction solution was cooled to −60° C.
  2. customreturned to room temperature
  3. stirringwhile stirring for 1 hour
  4. washwashed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under a reduced pressure
  7. additionthe thus obtained residue was mixed with diisopropyl ether (20 ml)
  8. filtrationthe thus precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-f73fc60e0a1345fab5e160e53239807e
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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