Reaction #964

Reaction equation

(3RS)-1-benzyl-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine

→

(3RS)-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine

Solvents

ethanol

Conditions

Workup

1. 1
   FiltrationAfter filtration of the catalyst
2. 2
   Otherthrough cellite and evaporation of the solvent
3. 3
   workup.ADDITIONTherefore 0.6 g of Pearlman's catalyst was added in 40 ml ethanol (95%) once more
4. 4
   workup.ADDITIONthe mixture was treated under H2 -atmosphere at 0.28 MPa over night
5. 5
   FiltrationFiltration
6. 6
   Otherthrough cellite and evaporation of the solvent
7. 7
   Othergave the product in a quantitative yield (2.18 g)

Procedure

3.1 g (0.0t mol) (3RS)-1-benzyl-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine was hydrogenated at 0.28 MPa over 0.6 g of Pearlman's catalyst (Pd(OH)2) in 40 ml ethanol (95%) over night. After filtration of the catalyst through cellite and evaporation of the solvent 1H-NMR showed that the reaction was not completed. Therefore 0.6 g of Pearlman's catalyst was added in 40 ml ethanol (95%) once more and the mixture was treated under H2 -atmosphere at 0.28 MPa over night. Filtration through cellite and evaporation of the solvent gave the product in a quantitative yield (2.18 g).

Source