Hydrochloric Acid → trans Ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)-ethyl]-pyrrolidine-2-carboxylate

HRID 345357Notes

Reaction equation

HRID 345357 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][O:13][CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:7]1[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:5])[CH3:2].C([Li])CCC.Cl>C(O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@@H:8]([CH2:11][CH2:12][O:13][CH2:14][O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:7]1[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 131716329cis Ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)ethyl]-pyrrolidine-2-carboxylateHCID 178418339Butyllithium

Product 1

HCID 131716330trans Ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)-ethyl]-pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.2 g of cis ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)-ethyl]-pyrrolidine-2-carboxylate in 75 ml of anhydrous ethanol containing 1 ml of butyllithium (1.6 M) is refluxed under nitrogen for 6 days. After cooling, 1.7 ml of 1N hydrochloric acid is added, the solution is concentrated in vacuo, cold water added and mixture extracted with methylene chloride. The extract is dried over sodium sulfate, filtered, concentrated and purified by high pressure liquid chromatography using ethyl acetate/hexane (15:85) to yield trans ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)-ethyl]-pyrrolidine-2-carboxylate.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution is concentrated in vacuo, cold water
  3. additionadded
  4. extractionmixture extracted with methylene chloride
  5. dry with materialThe extract is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-41939d398eff48279ebc3461892ce13f
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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