Tetrahydrofuran → HCID 68006101, compound

HRID 1026552Notes

Reaction equation

HRID 1026552 reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:8]=[C:9]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[C:10]([CH2:13][CH2:14][C:15]([O:17]CC)=O)=[N:11][CH:12]=1.CC(C)([O-])C.[K+]>O>[Cl:6][C:7]1[CH:8]=[C:9]2[C:10]([CH2:13][CH2:14][C:15](=[O:17])[N:20]2[CH:21]2[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[CH2:25][CH2:26]2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 68006298HCID 68006298, compound

Product 1

HCID 68006101HCID 68006101, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice cooling, to a tetrahydrofuran solution (500 ml) of tert-butyl 4-{[5-chloro-2-(3-ethoxy-3-oxopropyl)pyridin-3-yl]amino}piperidine-1-carboxylate (54.7 g) was added dropwise a tetrahydrofuran solution (1 M, 159 ml) of potassium tert-butoxide over 15 minutes. After stirring for 15 minutes at the same temperature, water was added to the reaction solution, and extracted with dichloromethane. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-chloro-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (31.2 g).

Workup

  1. additionwas added to the reaction solution
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fee3d323d83149ecac4be56e6d217a54
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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