Tert-butyl[3-(5-benzyloxy-2-nitrophenoxy)benzyl]carbamate → Tert-butyl[3-(2-amino-5-hydroxyphenoxy)benzyl]carbamate

HRID 1373220Notes

Reaction equation

HRID 1373220 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[C:20]([O:22]CC3C=CC=CC=3)[CH:19]=[CH:18][C:17]=2[N+:30]([O-])=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=2[NH2:30])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 21073109Tert-butyl[3-(5-benzyloxy-2-nitrophenoxy)benzyl]carbamate

Product 1

HCID 21073107Tert-butyl[3-(2-amino-5-hydroxyphenoxy)benzyl]carbamateYield 98.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% carbon-palladium (3.2 g) was added to an ethyl acetate (300 ml) solution of tert-butyl[3-(5-benzyloxy-2-nitrophenoxy)benzyl]carbamate (10.5 g, 23.3 mmols). The resulting mixture was hydrogenated at room temperature under atmospheric pressure. The catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure to give a brown oil of tert-butyl[3-(2-amino-5-hydroxyphenoxy)benzyl]carbamate (7.6 g, 98.8%).

Workup

  1. customwas hydrogenated at room temperature under atmospheric pressure
  2. customThe catalyst was removed through filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8594ec69f87943be9b2f8a795fea13fc
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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