5-[3'-(t-Butoxycarbonylamino)propyloxy]-8-nitro-1,2,3,4-tetrahydronaphthalen-1-one → 8-Amino-5-[3'-(t-butoxycarbonylamino)propyloxy]-1,2,3,4-tetrahydronaphthalen-1-one

HRID 443025Notes

Reaction equation

HRID 443025 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:13]([O:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:14]2[C:19]=1[C:18](=[O:26])[CH2:17][CH2:16][CH2:15]2

Participants

4

Reactant 1

HCID 154058125-[3'-(t-Butoxycarbonylamino)propyloxy]-8-nitro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 154058138-Amino-5-[3'-(t-butoxycarbonylamino)propyloxy]-1,2,3,4-tetrahydronaphthalen-1-oneYield 109.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5-[3'-(t-Butoxycarbonylamino)propyloxy]-8-nitro-1,2,3,4-tetrahydronaphthalen-1-one (3.55 g) is dissolved in ethanol (160 ml), and thereto is added 10% palladium-carbon (420 mg). The mixture is stirred under hydrogen atmosphere for 1.5 hour, and the catalyst is removed by filtration. The filtrate is concentrated, and the residue is purified by silica gel column chromatography to give the title compound (3.56 g) as a yellow oil.

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationThe filtrate is concentrated
  3. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c33e40d69a9942e2ade5d247580c08f2
Source dataset
uspto-grants-1999_04
Patent number
US05892043

Reaction notes

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