Benzaldehyde → (S)-3-Benzylideneamino-2-oxo-1-piperidineacetic acid, Ethyl ester

HRID 1941446Notes

Reaction equation

HRID 1941446 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]1=[O:14].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH:15](=[N:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]1=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 13556450(S)-3-Amino-2-oxo-1-piperidineacetic acid, Ethyl ester

Product 1

HCID 86751787(S)-3-Benzylideneamino-2-oxo-1-piperidineacetic acid, Ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 22 (4.7586 g, 0.0200 mol) and benzaldehyde (2.1224 g, 0.0200 mol, 2.03 mL) in 50 mL CH2Cl2 at 0° under N2 was added anhydrous MgSO4 (5.0 g) and Et33N (4.05 g, 0.040 mol, 5.58 mL). The mixture was stirred from 0° to ambient temperature over 21 hrs, filtered under N2, and the solvent was evaporated. The residue was dissolved in 300 mL of diethyl ether, extracted with 50 mL portions of water (3×), brine, dried over MgSO4, filtered under N2 and evaporated to afford 5.13 g (89% yield) of product 23 as a light yellow viscous oil. The material was hydrolytically labile and was stored at 0° under a N2 atmosphere.

Workup

  1. filtrationfiltered under N2
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 300 mL of diethyl ether
  4. extractionextracted with 50 mL portions of water (3×), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered under N2
  7. customevaporated

Sources & evidence

ORD record
ord-4e845ac07a8541a8881d14ee867b01f3
Source dataset
uspto-grants-1997_12
Patent number
US05703208

Reaction notes

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