Reaktion #93054

Reaktionsgleichung

triethylamine

N-benzyloxycarbonyl-L-proline

methyl 1-aminocyclopentane-1-carboxylate

dioxane

water

→

methyl N-benzyloxy-carbonyl-L-prolyl-1-aminocyclopentane-1-carboxylate

Ausbeute 79.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere then added
2. 2
   Waschenthe organic phase was washed successively with 10% strength aqueous citric acid solution, sodium carbonate solution and water
3. 3
   Trocknendried over sodium sulfate
4. 4
   Sonstigeevaporated down under reduced pressure
5. 5
   SonstigeCrystallization of the solid residue

Vorschrift

5.4 ml of triethylamine and 13.5 g of the N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-proline were added to 5.6 g of methyl 1-aminocyclopentane-1-carboxylate in 50 ml of dioxane at 10° C., the reaction mixture was stirred for 2 hours at this temperature, 20 ml of water were then added and the reaction was allowed to continue for 20 hours at room temperature. The mixture was taken up in ethyl acetate, and the organic phase was washed successively with 10% strength aqueous citric acid solution, sodium carbonate solution and water, dried over sodium sulfate and evaporated down under reduced pressure. Crystallization of the solid residue gave 11.5 g (79%) of methyl N-benzyloxy-carbonyl-L-prolyl-1-aminocyclopentane-1-carboxylate.

Quelle