Reacción #487519

ord-1ee5c601f41b440988e9b2344cb109b8

Ecuación de reacción

N
ammonia
O=c1ccc2ccc(OCCC3CO3)cc2o1
racemic 4-(7-coumarinyloxy)-1,2-epoxybutane
NCC(O)CCOc1ccc2ccc(=O)oc2c1
amine
Rendimiento 50.0%
NCC(O)CCOc1ccc2ccc(=O)oc2c1
1-Amino-4-(7-coumarinyloxy)-2-butanol
Rendimiento 50.0%

Disolventes

Condiciones de reacción

Temperatura
65°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe solvent is evaporated
  2. 2
    workup.ADDITIONthe residue is diluted in ethyl acetate
  3. 3
    Lavadoit is washed with an NaCl-saturated solution

Procedimiento

5 ml of 30% aqueous ammonia and Gd (OTf3) (0.039 g, 0.065 mmol) are added to a solution of racemic 4-(7-coumarinyloxy)-1,2-epoxybutane (0.150 g, 0.65 mmol) in 2 ml of ethanol. It is heated at 65° C. for 15 hours, the solvent is evaporated, the residue is diluted in ethyl acetate, and it is washed with an NaCl-saturated solution. The residue provides the crude amine (0.081 g, yield 50%) that is used without purification for the next stage.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08741593B2uspto-grants-2014_06