Potassium tert-butoxide → Methyl 1-benzyl-2-methyl-3-oxopiperidine-4-carboxylate

HRID 1971350Notes

Reaction equation

HRID 1971350 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:8]([C:10]([O:12]CC)=O)[CH3:9].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][CH2:6][N:7]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:8]([CH3:9])[C:10]1=[O:12])=[O:22]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 67423852Methyl 4-(benzyl(1-ethoxy-1-oxopropan-2-yl)amino)butanoate

Product 1

HCID 67423405Methyl 1-benzyl-2-methyl-3-oxopiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[benzyl-(1-ethoxycarbonyl-ethyl)-amino]-butyric acid methyl ester (1.5 g, 4.9 mmol), potassium tert-butoxide (906 mg, 8.9 mmol) and toluene (100 mL) is stirred at rt for 3 h. The mixture is then partitioned between DCM and saturated aqueous NH4Cl. The organic layer is removed, dried over anhydrous Na2SO4, and concentrated. The crude residue is used without further purification. MS (ESI) m/z 262.2 (M+1).

Workup

  1. customThe mixture is then partitioned between DCM and saturated aqueous NH4Cl
  2. customThe organic layer is removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue is used without further purification

Sources & evidence

ORD record
ord-71da6ccaf14f46f0b2c7d7ac63d050c0
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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