Sodium hydride → HCID 11015313, compound

HRID 1106914Notes

Reaction equation

HRID 1106914 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 110667371,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Product 1

HCID 11015313HCID 11015313, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-benzyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (3.06 g, 10.0 mmol) in dry DMF (30 ml) was added dropwise to a slurry of sodium hydride (60% dispersion in oil/480 mg, 12.0 mmol) in dry DMF (20 ml) under nitrogen at room temperature. The reaction mixture was stirred for one hour at room temperature to which was added dropwise tert-butyl bromoacetate (1.48 ml, 10.0 mmol). The reaction was stirred for a further two hours, diluted with ethyl acetate (100 ml), washed with brine (2×100 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by chromatography on silica gel with ethyl acetate-hexane (2:5) as eluant. (3.28 g, 78%).

Workup

  1. stirringThe reaction was stirred for a further two hours
  2. washwashed with brine (2×100 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-c7662ca30dd241a28693ee060dbb9cf6
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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