Ethyl bromoacetate → Ethyl 3-methoxycarbonyl-4-oxo-1-piperidineacetate

HRID 964979Notes

Reaction equation

HRID 964979 reaction equation
Cl.[O:2]=[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([O:11][CH3:12])=[O:10].C(=O)([O-])O.[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(OCC)(=O)C>O.C(OCC)C>[CH3:12][O:11][C:9]([CH:4]1[C:3](=[O:2])[CH2:8][CH2:7][N:6]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:5]1)=[O:10]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724028Methyl 4-oxopiperidine-3-carboxylate hydrochloride

Product 1

HCID 53727806Ethyl 3-methoxycarbonyl-4-oxo-1-piperidineacetateYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

1.94 g of methyl 4-oxo-3-piperidinecarboxylate hydrochloride, 1.68 g of sodium hydrogencarbonate and 1.67 g of ethyl bromoacetate were dissolved in a mixed solvent comprising 32 ml of water and 8 ml of diethyl ether and stirred at room temperature overnight. 50 ml of ethyl acetate was added to the reaction liquid, and the organic layer was separated by liquid-liquid separation. This was dried with sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (using a gradient eluent of chloroform to chloroform/methanol=100/1) to obtain 1.5 g of ethyl 3-methoxycarbonyl-4-oxo-1-piperidineacetate as an oily substance.

Workup

  1. customthe organic layer was separated by liquid-liquid separation
  2. dry with materialThis was dried with sodium sulfate
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-55597e8f771145909bfdedf880f43ae4
Source dataset
uspto-grants-1998_06
Patent number
US05773442

Reaction notes

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