Water → HCID 9839330, compound

HRID 963335Notes

Reaction equation

HRID 963335 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([C:21]([O:23]CC)=[O:22])[C:16]([O:18]CC)=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].C1COCC1.O>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH:15]([C:16]([OH:18])=[O:17])[C:21]([OH:23])=[O:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 21180611Diethyl {[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}propanedioate

Product 1

HCID 9839330HCID 9839330, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(tert-Butoxycarbonyl)-4-[2,2-di(ethoxycarbonyl)ethyl]piperidine (12.2 g, 34 mmol), prepared as in Example 1, Step (b), and potassium hydroxide (4.2 g, 75 mmol) were combined in ethanol (10 mL), THF (20 mL), and water (50 mL) and the mixture was heated at reflux for 3 hours. The mixture was cooled and washed with ether, acidified with sulfuric acid, and extracted into ether. The ether was dried over sodium sulfate and evaporated. Crystallization of the residue from ether gave 1-(tert-butoxycarbonyl)-4-[2,2-di(carboxy)ethyl]piperidine (8.5 g, 28 mmol) which was heated in an oil bath to 165° C. until evolution of CO2 ceased (approximately 10 minutes). The residue was cooled and upon crystallization gave 3-[l-(tert-butoxycarbonyl)piperidin-4-yl]propionic acid (7.2 g, 28 mmol), m.p. 81°-83° C.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe mixture was cooled
  3. washwashed with ether
  4. extractionextracted into ether
  5. dry with materialThe ether was dried over sodium sulfate
  6. customevaporated
  7. customCrystallization of the residue from ether

Sources & evidence

ORD record
ord-a90ff5856e6141d4b5971f223c411dc0
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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