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 1167401Notes

Reaction equation

HRID 1167401 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-68144b08315f498ab4d63a6e62c08498
Source dataset
uspto-grants-2003_09
Patent number
US06617456B1

Reaction notes

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