Water → cis 1-Ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol

HRID 1164889Notes

Reaction equation

HRID 1164889 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][CH:8]([CH2:11][C:12](O)=[O:13])[CH:7]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])[CH3:2].B.O1CCCC1.O>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][OH:13])[C@@H:7]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 197578301-Ethoxycarbonyl-2-ethoxycarbonyl-pyrrolidine-3-acetic acid

Product 1

HCID 86743786cis 1-Ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10 g of 1-ethoxycarbonyl-2-ethoxycarbonyl-pyrrolidine-3-acetic acid in 50 ml tetrahydrofuran is cooled to 0° and 55 ml of borane/tetrahydrofuran (1M) is added dropwise. After stirring 2 hours at 0°, 20 ml of water is added, the mixture is extracted with ethyl acetate, washed twice with water and dried over sodium sulfate. The solution is filtered, concentrated and purified by flash chromatography using ethyl acetate/hexane (1:1 to 7:3) to yield cis 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washwashed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution is filtered
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-93b851fb61e84b19a037f8957f486a97
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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