Sodium hydride → 2-Tert-butoxycarbonyl-9-methoxycarbonylmethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole

HRID 2301083Notes

Reaction equation

HRID 2301083 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Product 1

HCID 110784542-Tert-butoxycarbonyl-9-methoxycarbonylmethyl-1,2,3,4-tetrahydropyrido[3,4-b]indoleYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 218 mg (5.45 mmol) portion of sodium hydride was added to 12 ml of DMF solution containing 0.99 g (3.64 mmol) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole, and the mixture was stirred at room temperature for 30 minutes, mixed with 0.52 ml (5.45 mmol) of methyl bromoacetate and again stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the thus obtained oily material was purified by a silica gel column chromatography (200 cc; elution by ethyl acetate-hexane=1:3) to obtain 0.96 g of the title compound (77% in yield).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was removed by evaporation under a reduced pressure
  5. customthe thus obtained oily material was purified by a silica gel column chromatography (200 cc; elution by ethyl acetate-hexane=1:3)

Sources & evidence

ORD record
ord-48e7c6cece6146d9ad727b3c6084e3cd
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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