Water → HCID 19969794, compound

HRID 36703Notes

Reaction equation

HRID 36703 reaction equation
[CH2:1]([N:8]=[C:9]([CH:11]1[CH:16]([C:17](O)=O)[CH2:15][CH:14]([CH3:20])[CH2:13][NH:12]1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH:11]2[CH:16]([CH2:15][CH:14]([CH3:20])[CH2:13][NH:12]2)[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178430573HCID 178430573, compound

Product 1

HCID 19969794HCID 19969794, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

13.0 g of crude 5-methyl-hexahydropyridine-2,3-dicarboxylic acid N-benzylimide are added in the form of a solution in 50 ml of absolute tetrahydrofuran to 4.6 g (0.12 mol) of lithium aluminum hydride in 100 ml of absolute tetrahydrofuran, already present in the vessel. Then the mixture is boiled for 17 hours under reflux. 4.6 g of water in 14 ml of tetrahydrofuran, 4.6 g of 10% strength sodium hydroxide solution and 13.8 g of water are added dropwise one after the other. The salts are filtered off, the filtrate is concentrated by evaporation and the residue is distilled.

Workup

  1. temperatureunder reflux
  2. filtrationThe salts are filtered off
  3. concentrationthe filtrate is concentrated by evaporation
  4. distillationthe residue is distilled

Sources & evidence

ORD record
ord-352dfc76302b4aa0b96f5e64bf68c735
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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