(1R,2S)-2-tert-Butoxycarbonylcyclopropanecarboxylic acid → Ethyl 3-(Cis-2-t-butoxycarbonylcyclopropyl)-3-oxopropionate

HRID 1936619Notes

Reaction equation

HRID 1936619 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@H:9]1[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@H:9]1[C:11](=[O:13])[CH2:8][C:6]([O:5][CH2:1][CH3:2])=[O:7])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 53929811(1R,2S)-2-tert-Butoxycarbonylcyclopropanecarboxylic acid

Product 1

HCID 53907535Ethyl 3-(Cis-2-t-butoxycarbonylcyclopropyl)-3-oxopropionateYield 128.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 100 ml of an anhydrous tetrahydrofuran solution of 7.56 g (40.6 mmol) of cis-2-t-butoxycarbonylcyclopropanecarboxylic acid was added 7.57 g (46.7 mmol) of 1,1-carbonyldiimidazole under cooling with ice. After stirring the mixture was stirred at room temperature for 2 hours, the solvent was evaporated under reduced pressure. To 50 ml of an anhydrous tetrahydrofuran solution of the resulting residue was added 80 ml of an anhydrous tetrahydrofuran solution of 101.5 mmol of previously prepared magnesium monoethyl malonate was added, followed by stirring overnight. After completion of the reaction, the solvent was removed by evaporation under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed successively with 0.5N hydrochloric acid, a saturated sodium hydrogencarbonate aqueous solution, and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to give 6.67 g (64.1%) of the titled compound as a yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringwas stirred at room temperature for 2 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo 50 ml of an anhydrous tetrahydrofuran solution of the resulting residue was added 80 ml of an anhydrous tetrahydrofuran solution of 101.5 mmol of previously prepared magnesium monoethyl malonate
  5. additionwas added
  6. stirringby stirring overnight
  7. customAfter completion of the reaction
  8. customthe solvent was removed by evaporation under reduced pressure, and ethyl acetate
  9. additionwas added to the residue
  10. washThe mixture was washed successively with 0.5N hydrochloric acid
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-77ad8fc495f54a4db747c96e03c716f7
Source dataset
uspto-grants-2002_05
Patent number
US06391889B1

Reaction notes

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