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 1636059Notes

Reaction equation

HRID 1636059 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-06175824018a4b8ca79fab5b49fb1687
Source dataset
uspto-grants-2003_01
Patent number
US06512118B1

Reaction notes

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