1-Azidomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-one → 1-Aminomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-one

HRID 2225490Notes

Reaction equation

HRID 2225490 reaction equation
[N:1]([CH2:4][C:5]12[CH2:12][CH2:11][C:8]([CH3:13])([CH2:9][CH2:10]1)[C:7](=[O:14])[O:6]2)=[N+]=[N-].[H][H]>C(O)C.[Pt](=O)=O>[NH2:1][CH2:4][C:5]12[CH2:12][CH2:11][C:8]([CH3:13])([CH2:9][CH2:10]1)[C:7](=[O:14])[O:6]2

Participants

5

Reactant 2

HCID 190047971-Azidomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 190047031-Aminomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-oneYield 84.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

0.025 g of platinum dioxide was added to a solution of 0.6 g of 1-azidomethyl-4-methyl-2-oxabicyclo[2.2.2]octan-3-one (Example 29) in 30 ml of ethanol. The resultant solution was reacted for 14 hours under 3.5 atom hydrogen gas. After reaction, the catalyst was filtered out, and the solvent was removed in vacuo from the filtrate. As a result, 0.44 g of 1-aminomethyl-4-methyl-2-oxabicyclo[2.2.2]-octan-3-one was obtained as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customAfter reaction
  2. filtrationthe catalyst was filtered out
  3. customthe solvent was removed in vacuo from the filtrate

Sources & evidence

ORD record
ord-651ea7f3fdfc4619b4c7a8a05981a4ef
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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