Propanal → Methyl (-)-(S)-1-propyl-2-pyrrolidinecarboxylate

HRID 129572

Reaction equation

HRID 129572 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH3:10])=[O:8].[CH:11](=O)[CH2:12][CH3:13].[H][H]>[Pd].CO>[CH2:11]([N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH3:10])=[O:8])[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 527PropanalHCID 2733200methyl L-prolinate hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 53820032Methyl (-)-(S)-1-propyl-2-pyrrolidinecarboxylateYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl (S)-2-pyrrolidinecarboxylate hydrochloride (1.65 g, 0.01 mol) was added to a hydrogenation flask containing a mixture of propionaldehyde (2.4 g, 0.04 mol), 5% Pd/C (0.3 g) and 30 ml MeOH. The mixture was shaken an a Parr apparatus at 40 psi hydrogen pressure for 2 h at room temperature. After filtration and evaporation the residue was mixed with 10 ml 2M HCl and 40 ml ice-water and then extracted twice with ET2O. Solid NaCl was added to the aqueous phase which was made alkaline with 20 ml 2M NH3 during addition of ice. Extraction with Et2O twice, drying (MgSO4) and evaporation afforded 1.8 g of the title compound, which was used directly in Example 11A. [α]D25 =-85° (c=1.3, CHCl3); MS (EI, 70 eV): m/z (rel.int.) 171(M, 1.9%), 112(100%).

Workup

  1. additioncontaining
  2. filtrationAfter filtration and evaporation the residue
  3. additionwas mixed with 10 ml 2M HCl and 40 ml ice-water
  4. extractionextracted twice with ET2O
  5. additionSolid NaCl was added to the aqueous phase which
  6. additionduring addition of ice
  7. extractionExtraction with Et2O twice
  8. customdrying
  9. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-503bfea50ebd4f6b9a3f475723b34ee1
Source dataset
uspto-grants-1995_11
Patent number
US05468876

Linked notes

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