Allyl bromide → N-Allyl-3-(t-Butoxycarbonylamino)isoxazole

HRID 1793664Notes

Reaction equation

HRID 1793664 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][O:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18]>C(COC)OC.O>[CH2:18]([N:10]1[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:13]=[CH:12][O:11]1)[CH:17]=[CH2:16]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 21992950tert-Butyl 1,2-oxazol-3-ylcarbamate

Product 1

HCID 22022967N-Allyl-3-(t-Butoxycarbonylamino)isoxazoleYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(t-Butoxycarbonylamino)isoxazole (12 g, 65.2 mM) was dissolved in dimethoxyethane (150 ml) and cooled to 0° C. under nitrogen. To the stirred solution was added sodium hydride (60% in oil, 2.87 g, 71.7 mM), and the mixture stirred 20 minutes. Allyl bromide (8.7 g, 71.7 mM) was added dropwise, and the mixture stirred at ambient temperature for 18 hours, then diluted with water (300 ml), and extracted into diethyl ether (3×100 ml). The extracts were washed with brine (100 ml), dried (magnesium sulfate), and chromatographed on silica (50 g) eluting with dichloromethane . Relevant fractions were combined to give the desired product as an oil (14.68 g). MS (ESP): 225 (MH+) for C11H16N2O3

Workup

  1. stirringthe mixture stirred at ambient temperature for 18 hours
  2. extractionextracted into diethyl ether (3×100 ml)
  3. washThe extracts were washed with brine (100 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customchromatographed on silica (50 g)
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-235e9784afc141d3be6661cba6cb882e
Source dataset
uspto-grants-2006_07
Patent number
US07081538B1

Reaction notes

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