Ethyl-[2-(4-nitro-phenoxy)-ethyl]-carbamic acid tert-butyl ester → [2-(4-Amino-phenoxy)-ethyl]-ethyl-carbamic acid tert-butyl ester

HRID 2415278Notes

Reaction equation

HRID 2415278 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:20][CH3:21])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)[CH2:20][CH3:21])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 23525785Ethyl-[2-(4-nitro-phenoxy)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 23525777[2-(4-Amino-phenoxy)-ethyl]-ethyl-carbamic acid tert-butyl esterYield 113.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl-[2-(4-nitro-phenoxy)-ethyl]-carbamic acid tert-butyl ester (825 mg, 2.36 mmol) (from step B above) and 150 mg of 10% palladium-on-carbon in ethanol (25 mL) was hydrogenated at 20 psi in a Parr shaker for 1 hour. The mixture was filtered through Celite™ and the solvent was evaporated to give 750 mg (100%) [2-(4-amino-phenoxy)-ethyl]-ethyl-carbamic acid tert-butyl ester.

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-27e2595afd194c8c9ae2682ae87a2edb
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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