HCID 89525592, compound → HCID 89525610, compound

HRID 1528154Notes

Reaction equation

HRID 1528154 reaction equation
[N:1]([CH:4]([C:11]1([CH2:15][F:16])[CH2:14][O:13][CH2:12]1)[C:5]1[O:6][C:7]([CH3:10])=[CH:8][CH:9]=1)=[N+]=[N-].[H][H]>C(O)C.[Pd]>[CH3:10][C:7]1[O:6][C:5]([CH:4]([NH2:1])[C:11]2([CH2:15][F:16])[CH2:12][O:13][CH2:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 89525592HCID 89525592, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89525610HCID 89525610, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.25 g (10 mmol, 1 eq) of 2-[azido-(3-fluoromethyloxetan-3-yl)methyl]-5-methylfuran in 40 ml of ethanol in the presence of 378 mg (17% by weight) of palladium on carbon at 10% was stirred at hydrogen atmospheric pressure for two and a half hours. The reaction medium was filtered and the filtrate was evaporated. 2.0 g of C-(5-methylfuran-2-yl)-C-(3-fluoromethyloxetan-3-yl)methylamine were obtained in the form of a grayish oil. Yield=100%. TLC SiO2/Heptane:EtOAc (70/30), developing with KMnO4.

Workup

  1. filtrationThe reaction medium was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a0644cb681d94fcc89b583f5796a13d4
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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