L-Proline → HCID 22626613, compound

HRID 351648Notes

Reaction equation

HRID 351648 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[C:23]([CH:24]=O)=[CH:22][CH:21]=[CH:20][N:19]=1.N1CCC[C@H]1C(O)=O>C(O)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:24][C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 22626613HCID 22626613, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3.14 g of 1-tert-butoxycarbonyl-4-acetyl-piperidine and 1.83 g of 2-amino-3-formyl-pyridine were refluxed with 0.25 g of L-proline in n-butanol for 72 hours. After removing the solvent in vacuo the residue was combined with the residue obtained in an identical reaction and chromatographed on silica gel with ethyl acetate/n-heptane (1:1) to give 1.08 g of the title compound.

Workup

  1. customAfter removing the solvent in vacuo the residue
  2. customobtained in an identical reaction
  3. customchromatographed on silica gel with ethyl acetate/n-heptane (1:1)

Sources & evidence

ORD record
ord-c07c0ab157704ac0969a79d74be51adb
Source dataset
uspto-grants-2004_06
Patent number
US06743800B1

Reaction notes

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