Water → 3-(1-((Benzyloxy)carbonyl)piperidin-4-yl)propanoic acid

HRID 484483Notes

Reaction equation

HRID 484483 reaction equation
[OH-].[K+].O.[C:4]1([CH2:10][O:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[CH2:16][CH2:15]2)=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[C:4]1([CH2:10][O:11][C:12]([N:14]2[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:18][CH2:19]2)=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 14989191Benzyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylate

Product 1

HCID 98953153-(1-((Benzyloxy)carbonyl)piperidin-4-yl)propanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred and cooled (15° C.) mixture of 11.1 parts of potassium hydroxide and 96 parts of water wa added dropwise a solution of 31.8 parts of ethyl 1-[(phenylmethoxy)carbonyl]-4-piperidinepropanoate in 38 parts of ethanol during 20 minutes. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was evaporated at <50° C. The reaction mixture was poured into crushed ice and treated with concentrated hydrochloric acid. The separated aqueous layer was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 29 parts (100%) of 1-[(phenylmethoxy)carbonyl]-4-piperidinepropanoic acid as a residue (int. 33).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. customThe reaction mixture was evaporated at <50° C
  5. additionThe reaction mixture was poured
  6. custominto crushed ice
  7. additiontreated with concentrated hydrochloric acid
  8. extractionThe separated aqueous layer was extracted with dichloromethane
  9. customThe extract was dried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-073f2d46a8ad45f1ad135a37e48d8563
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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