Hydrochloric Acid → HCID 23079664, compound

HRID 2112755Notes

Reaction equation

HRID 2112755 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)([C:14]([O:16]CC)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69001884HCID 69001884, compound

Product 1

HCID 23079664HCID 23079664, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(tert-butoxycarbonyl)-4-(3-pyrrolidin-1-ylpropyl)piperidine-4-carboxylate (0.12 g, 0.33 mmol) prepared according to Process Step 2 was mixed with ethanol (1.8 mL) and aqueous sodium hydroxide solution (2.0 mol/L, 1.6 mL, 3.3 mmol), followed by stirring under reflux for fifteen hours. After adjusting the pH to 7.8 by adding diluted hydrochloric acid (6.0 mol/L) added under ice-cooling, the reaction mixture was extracted with n-butanol. The organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was dried under reduced pressure and thereby yielded 1-(tert-butoxycarbonyl)-4-(3-pyrrolidin-1-ylpropyl)piperidine-4-carboxylic acid (0.10 g, 91%).

Workup

  1. temperatureunder reflux for fifteen hours
  2. additionadded under ice-
  3. temperaturecooling
  4. extractionthe reaction mixture was extracted with n-butanol
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-a9ee20c84ebd4c99ae6a706ef506cdfd
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

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