3-(Azidomethyl)-5-(furan-2-yl)-1,2-oxazole → 5-(2-Furanyl)-3-isoxazolemethanamine

HRID 606286Notes

Reaction equation

HRID 606286 reaction equation
[N:1]([CH2:4][C:5]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[O:7][N:6]=1)=[N+]=[N-]>CO.[Pd]>[O:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[C:8]1[O:7][N:6]=[C:5]([CH2:4][NH2:1])[CH:9]=1

Participants

4

Reactant 1

HCID 576962103-(Azidomethyl)-5-(furan-2-yl)-1,2-oxazole

Product 1

HCID 70605335-(2-Furanyl)-3-isoxazolemethanamineYield 63.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.50 g of 3-azidomethyl-5-furan-2-yl-isoxazole and 600 mg of 5% palladium in 50 ml of methanol was stirred for 15 hrs under hydrogen atmosphere and then filtered. The filtrate was concentrated in vacuo to provide 821 mg of C-(5-furan-2-yl-isoxazol-3-yl)-methylamine (Step 3 Yield 59%). This concentrate was used in the next step without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8f4cd33f8e3d4cdf96ecd9cd18d14edb
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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