1-(3-Nitro-benzyl)-azetidine-3-carboxylic acid methyl ester → 1-(3-Amino-benzyl)-azetidine-3-carboxylic acid methyl ester

HRID 1629697Notes

Reaction equation

HRID 1629697 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[CH2:6]1)=[O:4]>CCO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=2)[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 575173161-(3-Nitro-benzyl)-azetidine-3-carboxylic acid methyl ester

Product 1

HCID 575173171-(3-Amino-benzyl)-azetidine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of INT 2 (250 mg, 0.99 mmol) in EtOH (10 mL) was added Pd—C 10% (25 mg). The mixture was stirred under 1 atm of H2 for 1 hour. The mixture was quenched with CH2Cl2 and filtered through a pad of Celite. The filtrate was concentrated to give INT 3.

Workup

  1. customThe mixture was quenched with CH2Cl2
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. customto give INT 3

Sources & evidence

ORD record
ord-ac2717e438084245a7d49f95f784ee84
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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