2-(2-(Ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline → 7-Amino-2-(2-(ethoxycarbonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 481769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481769
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N+:18]([O-])=O)=[CH:13][CH:14]=2)[CH2:9]1)=[O:5])[CH3:2]>C(O)C.[H][H].[C].[Pd]>[NH2:18][C:12]1[CH:11]=[C:10]2[C:15]([CH2:16][CH2:17][N:8]([CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:9]2)=[CH:14][CH:13]=1

Komponenten

5

Edukt 1

HCID 190671552-(2-(Ethoxycarbonyl)ethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 190671517-Amino-2-(2-(ethoxycarbonyl)ethyl)-1,2,3,4-tetrahydroisoquinolineAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 178418361HCID 178418361, VerbindungLösungsmittel

Versuchsvorschrift

1.1 g of 2-(2-(ethoxycarbonyl)ethyl)-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-(2-(ethoxycarbonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline, which was an oily product. This product with no further purification was dissolved in 10 ml of DMF, and 1.3 g of 1-(benzyloxycarbonyl)-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-(2-(ethoxycarbonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline (yield: 90%, oily product).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b5106d20e35e4357821dac158f15c575
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789595

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