Potassium Hydroxide → (1R,2S)-2-tert-Butoxycarbonylcyclopropanecarboxylic acid

HRID 498115Notes

Reaction equation

HRID 498115 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:7][C@H:6]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:4].[OH-].[K+]>CO>[C:11]([O:10][C:8]([C@H:6]1[CH2:7][C@H:5]1[C:3]([OH:4])=[O:2])=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53746334t-Butyl Cis-2-methoxycarbonylcyclopropanecarboxylate

Product 1

HCID 53929811(1R,2S)-2-tert-Butoxycarbonylcyclopropanecarboxylic acidYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 100 ml of a methanol solution of 9.49 g (47.4 mmol) of t-butyl cis-2-methoxycarbonylcyclopropanecarboxylate was added 40 ml of an aqueous solution of 4.06 g (61.5 mmol) of potassium hydroxide under cooling with ice, followed by stirring at room temperature for 24 hours. After completion of the reaction, the solvent was evaporated under reduced pressure. Water was added to the residue, and the mixture was washed with diethyl ether. The aqueous layer was adjusted to a pH of 2 to 3 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 7.56 g (85.7%) of the title compound as a pale yellow solid.

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater was added to the residue
  5. washthe mixture was washed with diethyl ether
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ee5141dd76f43a3a571b904a59b5173
Source dataset
uspto-grants-2005_09
Patent number
US06949662B2

Reaction notes

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