Reaction #5980

Reaction equation

ethylchloroformate

3-aminoquinuclidine dihydrochloride

1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid

triethylamine

→

1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran

Solvents

water

chloroform

chloroform

chloroform

Conditions

Workup

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITis continued overnight
3. 3
   Otherthe two layers separated
4. 4
   Washthe chloroform layer washed twice with water
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated to dryness

Procedure

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.

Source