Acetaldehyde → HCID 13504017, compound

HRID 35525Notes

Reaction equation

HRID 35525 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11](N)[CH:10](C)[C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16](=O)[CH3:17].Cl>[Pd].O>[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:9][N:8]([CH2:16][CH3:17])[CH2:1][CH3:2])[CH2:10][C:9]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 19354255(-)-1-Benzyl-4-amino-methyl-pyrrolidin-2-one

Product 1

HCID 13504017HCID 13504017, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 11.5 g (0.056 mol) of (-)-1-benzyl-4-amino-methyl-pyrrolidin-2-one, 130 ml of water, 13 g of acetaldehyde, 5.8 ml of concentrated hydrochloric acid and 6.5 g of 20% palladium-on-charcoal was hydrogenated for 51/4 hours at 5 bar and at 25° C. The reaction mixture was filtered, the filtrate was evaporated, the residue was taken up in 30 ml of water, and the solution was extracted with methylene chloride. The aqueous hydrochloric acid solution was made alkaline and then extracted with methylene chloride. By distillation of the combined extracts in a bulbed tube, 11.2 g (76.4% of theory) of the title compound were obtained, αD =-9.4 (c =1.0; :ethanol).

Workup

  1. custom4 hours
  2. customat 25° C
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated
  5. extractionthe solution was extracted with methylene chloride
  6. extractionextracted with methylene chloride
  7. distillationBy distillation of the combined extracts in a bulbed tube

Sources & evidence

ORD record
ord-b2cb560d82164e9da8fede7bfd89bc86
Source dataset
uspto-grants-1988_08
Patent number
US04767759

Reaction notes

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