1-Boc-4-Cbz-amino-piperidine → 4-Cbz-aminopiperidine

HRID 43823Notes

Reaction equation

HRID 43823 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.O1CCOCC1>[NH:15]1[CH2:14][CH2:13][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Participants

3

Reactant 1

HCID 15143051-Boc-4-Cbz-amino-piperidine

Product 1

HCID 15143044-Cbz-aminopiperidineYield 86.5%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A 4 N hydrochloric acid/1,4-dioxane solution (20 mL) was added to tert-butyl 4-benzyloxycarbonylaminopiperidine-1-carboxylate obtained in Example (192a) (1.5 g, 4.49 mmol). The mixture was stirred at room temperature for one hour, and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in methanol. Amberlite IRA-400(Cl) ion exchange resin (20 g) was added, and the mixture was stirred at room temperature for one hour. Amberlite was filtered off, and then the solution was concentrated under reduced pressure to obtain 910 mg of the title compound as a colorless oily substance.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in methanol
  3. additionAmberlite IRA-400(Cl) ion exchange resin (20 g) was added
  4. stirringthe mixture was stirred at room temperature for one hour
  5. filtrationAmberlite was filtered off
  6. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7dfe09480b5c42da964ce9a8880e196e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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