4-[Azido-(5-methylfuran-2-yl)methyl]tetrahydropyran → (5-Methylfuran-2-yl)(tetrahydro-2H-pyran-4-yl)methanamine

HRID 2271505Notes

Reaction equation

HRID 2271505 reaction equation
[N:1]([CH:4]([C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[N+]=[N-].[H][H]>C(O)C.[Pd]>[CH3:16][C:13]1[O:12][C:11]([CH:4]([NH2:1])[CH:5]2[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 895254354-[Azido-(5-methylfuran-2-yl)methyl]tetrahydropyranHCID 178418361HCID 178418361, compound

Product 1

HCID 62907069(5-Methylfuran-2-yl)(tetrahydro-2H-pyran-4-yl)methanamineYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.09 g (14 mmol, 1 eq) of 4-[azido-(5-methylfuran-2-yl)methyl]tetrahydropyran in 60 ml of ethanol in the presence of 470 mg (15% by weight) of palladium on carbon at 10% was stirred at hydrogen atmospheric pressure for 17 hours. The reaction medium was filtered and the filtrate was evaporated. 2.715 g of C-(5-methylfuran-2-yl)-C-(tetrahydropyran-4-yl)methylamine were obtained. Yield=99%.

Workup

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

Sources & evidence

ORD record
ord-2faee2d9398044bb98899e9b0383666d
Source dataset
uspto-grants-2015_09
Patent number
US09120772B2

Reaction notes

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