Potassium Hydroxide → HCID 13363165, compound

HRID 1979986Notes

Reaction equation

HRID 1979986 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15]CC)=[O:14])[N:9]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:7])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[N:9]1[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 6932551diethyl (2R,5R)-1-benzylpyrrolidine-2,5-dicarboxylate

Product 1

HCID 13363165HCID 13363165, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Potassium hydroxide (6.7 g, 0.1 m) in ethanol (180 ml) was slowly added to a solution of trans-1-benzyl-2,5-pyrrolidine dicarboxylic acid diethyl ester in ethanol (300 ml) at room temperature. This was stirred for 36 hours. The solvent was evaporated off and the residue dissolved in water. The pH of the solution was adjusted to 8 with dilute hydrochloric acid and the solution extracted with hexane to remove the unreacted amino diester. The aqueous solution was adjusted to a pH of 5.3 and was then extracted with diethyl ether. The combined extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated, giving 18.3 g (65%) of the title compound as an oil.

Workup

  1. customThe solvent was evaporated off
  2. dissolutionthe residue dissolved in water
  3. extractionthe solution extracted with hexane
  4. customto remove the unreacted amino diester
  5. extractionwas then extracted with diethyl ether
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d71a9550c04647a692af904498594f4c
Source dataset
uspto-grants-1984_11
Patent number
US04483991

Reaction notes

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