Reacción #5980

ord-16679a0222a54903abc287b1b5d2fb96

Ecuación de reacción

CCOC(=O)Cl
ethylchloroformate
Cl.Cl.NC1CN2CCC1CC2
3-aminoquinuclidine dihydrochloride
Nc1c(Cl)cc(C(=O)O)c2c1C1CCCCC1O2
1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid
CCN(CC)CC
triethylamine
Nc1c(Cl)ccc2c1C1CCCCC1O2
1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGStirring
  2. 2
    workup.WAITis continued overnight
  3. 3
    Otrothe two layers separated
  4. 4
    Lavadothe chloroform layer washed twice with water
  5. 5
    Secadodried over magnesium sulfate
  6. 6
    Filtraciónfiltered
  7. 7
    Otroevaporated to dryness

Procedimiento

To a cold solution of 0.3 g 1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid in 40 ml chloroform is added 0.3 g of triethylamine and then 0.2 g ethylchloroformate in 10 ml chloroform. Stirring is continued for 2 hours. This is then added to a cold mixture of 3 g 3-aminoquinuclidine dihydrochloride in 20 ml water containing 7.5 g K2CO3. Stirring is continued overnight. The reaction mixture is then diluted with chloroform, the two layers separated and the chloroform layer washed twice with water, dried over magnesium sulfate, filtered and evaporated to dryness to give 1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-(N-1-azabicyclo [2.2.2.]oct-3-yl)carboxamide as an oily Product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05246942uspto-grants-1993_09