(3RS)-1-benzyl-3-(N-tert-butyloxycarbonylaminoethyl)pyrrolidine → tert-butyl N-[2-(pyrrolidin-3-yl)ethyl]carbamate

HRID 868

Reaction equation

HRID 868 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 1

HCID 54496804(3RS)-1-benzyl-3-(N-tert-butyloxycarbonylaminoethyl)pyrrolidine

Product 1

HCID 21955469tert-butyl N-[2-(pyrrolidin-3-yl)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

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).

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthrough cellite and evaporation of the solvent
  3. additionTherefore 0.6 g of Pearlman's catalyst was added in 40 ml ethanol (95%) once more
  4. additionthe mixture was treated under H2 -atmosphere at 0.28 MPa over night
  5. filtrationFiltration
  6. customthrough cellite and evaporation of the solvent
  7. customgave the product in a quantitative yield (2.18 g)

Sources & evidence

ORD record
ord-2326e4f1e4844936a51646b96ee23d0d
Source dataset
uspto-grants-1998_03
Patent number
US05723444

Linked notes

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