Ethyl Acetate → HCID 54449227, compound

HRID 1789845Notes

Reaction equation

HRID 1789845 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:28])[CH:7]([CH:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH3:14])[C:8]([O:10]CC)=[O:9])[CH3:4].CCOC(C)=O>CCO.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:28])[CH:7]([CH:13]([CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:19][CH2:20]1)[CH3:14])[C:8]([OH:10])=[O:9])[CH3:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 53863445HCID 53863445, compound

Product 1

HCID 54449227HCID 54449227, compoundYield 119.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of KOH (84 mg, 1.16 mmol) in EtOH (2 mL) was added dropwise to a solution of 2-[1-(1-tert-butoxycarbonyl-piperidin-4-yl)-ethyl]-malonic acid diethyl ester (0.39 g, 1.01 mmol) in methylene chloride (4 mL) and EtOH (10 mL) at 0° C. The resulting mixture was stirred at room temperature over night. EtOAc was added and the mixture was washed with 0.5 M HCl and brine, dried and concentrated under reduced pressure to give 416 mg of crude 2-[1-(1-tert-butoxycarbonyl-piperidin-4-yl)-ethyl]-malonic acid monoethyl ester.

Workup

  1. washthe mixture was washed with 0.5 M HCl and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c37643589f614cb7846bdd883ea6da7d
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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