Sodium Hydroxide → HCID 53788865, compound

HRID 1457979Notes

Reaction equation

HRID 1457979 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([C:16]2([C:19]([O:21]CC)=[O:20])[CH2:18][CH2:17]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([C:16]2([C:19]([OH:21])=[O:20])[CH2:17][CH2:18]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54012988Ethyl 1-(1-benzyloxycarbonyl-3-(R)-pyrrolidinyl)cyclopropanecarboxylate

Product 1

HCID 53788865HCID 53788865, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 5.26 g (16.6 mmol) portion of ethyl 1-(1-benzyloxycarbonyl-3-(R)-pyrrolidinyl)cyclopropanecarboxylate was dissolved in 300 ml of ethanol, and the solution was cooled in an ice bath, mixed with 16.6 ml of 10N sodium hydroxide aqueous solution and then stirred at room temperature for 5 days. After completion of the reaction, ethanol was evaporated, and the remaining water layer was then acidified with hydrochloric acid and extracted with diethyl ether (50 ml×4). The organic layers were combined and dried over magnesium sulfate and then the solvent was evaporated to yield 4.95 g of the title compound quantitatively as an oily substance.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customwas evaporated
  3. extractionextracted with diethyl ether (50 ml×4)
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6f7834ab1f334de690b28bb489eea92c
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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