(R)-2-azido-1-benzylethylamine → (2R)-3-Phenylpropane-1,2-diamine

HRID 650677Notes

Reaction equation

HRID 650677 reaction equation
[N:1]([CH2:4][C@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][C@H:5]([NH2:13])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 14802497(R)-2-azido-1-benzylethylamine

Product 1

HCID 12699299(2R)-3-Phenylpropane-1,2-diamineYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A sample of the compound from step 3d (1.2 g, 6.8 mmole) was hydrogenated (4 atm) in ethanol over 1.2 g of 10% Pd/C for 21.5 hours at room temperature. The mixture was filtered to remove the catalyst, and the solvent was removed to afford the title compound (1.055 g). MS m/z (M+H)+: 151, MS m/z (M+NH4)+: 168.

Workup

  1. customfor 21.5 hours
  2. customat room temperature
  3. filtrationThe mixture was filtered
  4. customto remove the catalyst
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-0e6fad3b9b6d48e99aba96743faa0b11
Source dataset
uspto-grants-2001_08
Patent number
US06274715B1

Reaction notes

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