5-(2',6'-Dichlorobenzyloxy)-4-hydroxy-3-nitropentanoic acid t-butyl ester → 3-amino-5-(2',6'-dichlorobenzyloxy)-4-hydroxypentanoic Acid T-Butyl Ester

HRID 2120627Notes

Reaction equation

HRID 2120627 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([N+:22]([O-])=O)[CH:9]([OH:21])[CH2:10][O:11][CH2:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[NH2:22][CH:8]([CH:9]([OH:21])[CH2:10][O:11][CH2:12][C:13]1[C:14]([Cl:20])=[CH:15][CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:25]

Participants

4

Reactant 1

HCID 542726345-(2',6'-Dichlorobenzyloxy)-4-hydroxy-3-nitropentanoic acid t-butyl ester

Product 1

HCID 699869763-amino-5-(2',6'-dichlorobenzyloxy)-4-hydroxypentanoic Acid T-Butyl EsterYield 101.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(2′,6′-dichlorobenzyloxy)-4-hydroxy-3-nitropentanoic acid t-butyl ester (2.213 g, 0.0056 mol) and wet Raney nickel (3.4 g) in methanol (150 mL) was stirred for 2 hours under a hydrogen balloon at room temperature. The reaction mixture was filtered through Celite and the filter cake was washed with methanol. The filtrate was concentrated and chased with methylene chloride to give the title product (2.078 g, 100%). TLC: (methanol/methylene chloride 1/9): Rf=0.21.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7645f37a77bd48c6bbec6f8c4826751b
Source dataset
uspto-grants-2004_02
Patent number
US06693096B2

Reaction notes

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