Lithium Hydroxide → trans-2-(Methylpropylcarbamoyl)-cyclo-propane carboxylic acid

HRID 20374Notes

Reaction equation

HRID 20374 reaction equation
[OH-].[Li+].C([O:5][C:6]([C@@H:8]1[CH2:10][C@H:9]1[C:11](=[O:17])[N:12]([CH3:16])[CH2:13][CH2:14][CH3:15])=[O:7])C>O1CCCC1>[CH3:16][N:12]([CH2:13][CH2:14][CH3:15])[C:11]([C@@H:9]1[CH2:10][C@H:8]1[C:6]([OH:7])=[O:5])=[O:17]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68561965trans-2-(Methylpropylcarbamoyl)-cyclopropane carboxylic acid ethyl ester

Product 1

HCID 68558722trans-2-(Methylpropylcarbamoyl)-cyclo-propane carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1 N lithium hydroxide (25.6 mL, 25.59 mmol) to a solution of trans-2-(methylpropylcarbamoyl)-cyclopropane carboxylic acid ethyl ester (1.02 g, 5.1194 mmol) in tetrahydrofuran (30 mL). Stir vigorously for 2 days at room temperature. Concentrate and treat with water (50 mL) and extract with diethyl ether (50 mL). Acidify the aqueous layer with 1 N hydrochloric acid (26 mL) and extract with diethyl ether (3×125 mL). Combine the organic extracts, dry (magnesium sulfate) and concentrate to give the title compound as a racemic mixture (0.84 g, 89%).

Workup

  1. concentrationConcentrate
  2. additiontreat with water (50 mL)
  3. extractionextract with diethyl ether (50 mL)
  4. extractionextract with diethyl ether (3×125 mL)
  5. dry with materialCombine the organic extracts, dry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-ad32ed6536cb4c1caa629890dcc73e16
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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