2-(Ethoxycarbonylmethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline → 7-Amino-2-(ethoxycarbonylmethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 481767Notes

Reaction equation

HRID 481767 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([N+:17]([O-])=O)=[CH:12][CH:13]=2)[CH2:8]1)=[O:5])[CH3:2]>C(O)C.[H][H].[C].[Pd]>[NH2:17][C:11]1[CH:10]=[C:9]2[C:14]([CH2:15][CH2:16][N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8]2)=[CH:13][CH:12]=1

Participants

5

Reactant 1

HCID 106116392-(Ethoxycarbonylmethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 106811977-Amino-2-(ethoxycarbonylmethyl)-1,2,3,4-tetrahydroisoquinolineYield 90.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

1.1 g of 2-(ethoxycarbonylmethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 20 ml of ethanol, and a catalytic amount of 10% palladium-carbon was added to the solution. The solution was stirred overnight in hydrogen atmosphere. The catalyst was separated by filtration and the solvent was distilled off under reduced pressure to obtain 0.88 g of 7-amino-2-(ethoxycarbonylmethyl)-1,2,3,4-tetrahydroisoquinoline, which was an oily product. This product with no further purification was dissolved in 10 ml of N,N-dimethylformamide (DMF), and 1.3 g of 1-(benzyloxy-carbonyl)-4-(carboxymethoxy)piperidine and 1.1 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide which have been separately synthesized were added to the solution. After adding water, the solution was extracted with ethyl acetate, washed with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride in this order, and dried with anhydrous sodium sulfate. After separating the desiccant by filtration, the product was purified by silica gel column chromatography to obtain 1.7 g of 7-[1-(benzyloxycarbonyl)piperidine-4-yloxyacetylamino]-2-(ethoxycarbonylmethyl)-1,2,3,4-tetrahydroisoquinoline. (Yield: 90%, oily product).

Workup

  1. customThe catalyst was separated by filtration
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-df2db9c1aaf7477d8dd7a58ebeaa9e25
Source dataset
uspto-grants-1998_08
Patent number
US05789595

Reaction notes

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