Potassium Hydroxide → 2-(1-Tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid monoethyl ester

HRID 1789893Notes

Reaction equation

HRID 1789893 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:26])[CH:7]([CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:26])[CH:7]([CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 540037602-(1-tert-Butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid diethyl ester

Product 1

HCID 536676182-(1-Tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid monoethyl esterYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of KOH (0.26 g; 4.6 mmol) in ethanol (7 mL) was added to a solution of 2-(1-tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid diethyl ester (1.52 g; 4.4 mmol) in ethanol (7 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, concentrated under reduced pressure and the residue was dissolved in water (500 mL). The aqueous layer was washed with diethyl ether, acidified to pH. 3 by 0.5 M HCl, and extracted with diethyl ether. The organic phase was dried and concentrated under reduced pressure to yield 2-(1-tert-butoxycarbonyl-pyrrolidin-3-ylmethyl)-malonic acid monoethyl ester (1.13 g, 81%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water (500 mL)
  3. washThe aqueous layer was washed with diethyl ether
  4. extraction3 by 0.5 M HCl, and extracted with diethyl ether
  5. customThe organic phase was dried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f8a9d8a25cad409b9d662986ef9f9bf4
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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