Réaction #2010582

Équation de réaction

methyl quinuclidin-3-ylideneacetate hydrochloride

hydrochloric acid

→

title compound

Rendement 95.3%

(±)-Quinuclidine-3-acetic acid hydrochloride

Rendement 95.3%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered through celite
2. 2
   Autreevaporated to dryness
3. 3
   workup.DISSOLUTIONThe residue was dissolved in concentrated hydrochloric acid (10 ml)
4. 4
   workup.ADDITIONtreated with a further 10 ml of concentrated hydrochloric acid
5. 5
   Températureheated at 80° C. for 6 hours
6. 6
   Autreevaporated to dryness
7. 7
   workup.WAITThe residue was kept under vacuum over P2O5 for 3 days

Mode opératoire

A mixture of methyl quinuclidin-3-ylideneacetate hydrochloride (Example 18, Step 1) (2 g), ethanol (50 ml), 2M hydrochloric acid (5 ml) and 10% Pd/C (1 g) was stirred for 24 hours under H2 at atmospheric pressure, filtered through celite and evaporated to dryness. The residue was dissolved in concentrated hydrochloric acid (10 ml). heated at 60° C. for 18 hours, treated with a further 10 ml of concentrated hydrochloric acid, heated at 80° C. for 6 hours and evaporated to dryness. The residue was kept under vacuum over P2O5 for 3 days to give the title compound as a white solid (1.8 g); MS (+ve ion electrospray) m/z 170 (MH+, 100%).

Source