Ethyl 5-(5-tert-butoxycarbonylaminomethyl-2-nitrophenyl)pent-4-enoate → 2-(4-Ethoxycarbonylbutyl)-4-tert-butoxycarbonylaminomethylaniline

HRID 862600Notes

Reaction equation

HRID 862600 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:25]([O-])=O)=[C:14]([CH:16]=[CH:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pt]=O>[CH2:23]([O:22][C:20]([CH2:19][CH2:18][CH2:17][CH2:16][C:14]1[CH:15]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH:11]=[CH:12][C:13]=1[NH2:25])=[O:21])[CH3:24]

Participants

5

Reactant 2

HCID 53964031Ethyl 5-(5-tert-butoxycarbonylaminomethyl-2-nitrophenyl)pent-4-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 196983622-(4-Ethoxycarbonylbutyl)-4-tert-butoxycarbonylaminomethylanilineYield 108%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 5-(5-tert-butoxycarbonylaminomethyl-2-nitrophenyl)pent-4-enoate (560 mg, 1.48 mmol) in ethyl acetate (20 mL) was hydrogenated over platinum oxide (100 mg) under atmospheric pressure of hydrogen at room temperature for 2.5 h. The mixture was passed through celite and the filtrate was concentrated to give 560 mg of the title compound (100%).

Workup

  1. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-22ab9fbb19a6431c959843ea78f7af95
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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