Water → HCID 68878306, compound

HRID 2103766Notes

Reaction equation

HRID 2103766 reaction equation
C([N:8]1[C@@H:12]([CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10][C@@H:9]1[CH2:16][CH2:17][CH3:18])C1C=CC=CC=1.C([O-])=O.[NH4+].O.[OH-].[Na+]>CO.[OH-].[OH-].[Pd+2]>[CH2:16]([C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:13][CH2:14][CH3:15])[NH:8]1)[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 68879945HCID 68879945, compound

Product 1

HCID 68878306HCID 68878306, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Dissolve 1.56 g trans-1-benzyl-2,5-dipropylpyrrolidine from the Step C above in 100 mL methanol and add 4.01 g ammonium formate and 156 mg Pd(OH)2/C. Let the reaction mixture stir under nitrogen over night. Filter the reaction mixture through Celite to remove the catalyst. Concentrate the filtrate under reduced pressure to give a white solid residue. Suspend it in a small amount of water, add 5 mL 5 N NaOH solution, extract with ether several times, wash the combined ether solution with saturated brine, dry over anhydrous Na2SO4, and evaporate to give the title compound as yellow liquid. 1H NMR (CDCl3, 500 MHz) 3.11˜3.16 (m, 2H), 1.91˜1.98 (m, 2H), 1.26˜1.50 (m, 10H), 0.93 (t, J=7.1 Hz, 6H). LC-MS: 1.89 min. (M+H=156.1).

Workup

  1. filtrationFilter the reaction mixture through Celite
  2. customto remove the catalyst
  3. concentrationConcentrate the filtrate under reduced pressure
  4. customto give a white solid residue
  5. extractionextract with ether several times
  6. washwash the combined ether solution with saturated brine
  7. dry with materialdry over anhydrous Na2SO4
  8. customevaporate

Sources & evidence

ORD record
ord-9f79d1da52ff42308cc408dd7105d0a7
Source dataset
uspto-grants-2009_08
Patent number
US07576122B2

Reaction notes

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