Potassium Hydroxide → HCID 66811476, compound

HRID 1099203Notes

Reaction equation

HRID 1099203 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1(C(OCC)=O)[C:15]([O:17]CC)=[O:16])(=[O:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([N:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:5]1[C:15]([OH:17])=[O:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11056701HCID 11056701, compound

Product 1

HCID 66811476HCID 66811476, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl 1-acetyl-3-phenylpyrrolidine-2,2-dicarboxylate (110.6 g, 331 mmol) in ethanol (500 ml) was added potassium hydroxide (55.7 g, 993 mmol). The reaction was allowed to stir at reflux for 8 h and was then concentrated. The residue was dissolved in water and extracted with EtOAc. The aqueous layer was cooled to 0° C., carefully acidified to pH 2-3 using conc HCl, and exhaustively extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to yield 1-acetyl-3-phenylproline as a solid (95%).

Workup

  1. temperatureat reflux for 8 h
  2. concentrationwas then concentrated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with EtOAc
  5. extractionexhaustively extracted with EtOAc
  6. dry with materialThe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e4bc14cce7b455b89fdc1e26b4266e1
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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