HCID 91345472, compound → HCID 68644151, compound

HRID 1159176Notes

Reaction equation

HRID 1159176 reaction equation
[N:1]([CH:4]([CH2:15][N:16]=[N+]=[N-])[CH2:5][N:6]([CH2:13][CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+]=[N-]>CO.[Pt](=O)=O>[CH2:13]([N:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:5][CH:4]([NH2:1])[CH2:15][NH2:16])[CH3:14]

Participants

4

Reactant 1

HCID 91345472HCID 91345472, compound

Product 1

HCID 68644151HCID 68644151, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of rac-(2,3-diazido-propyl)-ethyl-phenyl-amine (0.245 g, 1 mmol) in methanol (5 ml) was added platinum(IV)-oxide (50 mg) and the mixture was hydrogenated at atmospheric pressure overnight. The catalyst was removed by filtration over celite and the filtrate was evaporated. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate) to yield a light yellow liquid (0.19 g, 98%); MS (ISP): 194.1 ((M+H)+).

Workup

  1. customwas hydrogenated at atmospheric pressure overnight
  2. customThe catalyst was removed by filtration over celite
  3. customthe filtrate was evaporated
  4. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate)

Sources & evidence

ORD record
ord-55be9197b000481981aa0c66a6d1769a
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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