Water → 3-Aminomethyl-1-N-Cbz-piperidine

HRID 2268946Notes

Reaction equation

HRID 2268946 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][N:18]=[N+]=[N-])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][NH2:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 15550580HCID 15550580, compound

Product 1

HCID 27564883-Aminomethyl-1-N-Cbz-piperidineYield 78.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolved 1-benzyloxycarbonyl-3-azidomethylpiperidine (1.27 g, 4.63 mmol, 1 eq) in THF (50 mL). Added water (10 mL). Added triphenylphosphine (1.5 g, 5.79 mmol, 1.25 eq) and let stir overnight. Removed solvent under reduced pressure and diluted the residue with 80 mL 1N HCl. Extracted the solution 3× with ethyl acetate to remove neutral organics. Basified the aqueous layer with 5N NaOH and extracted 3× with ethyl acetate. Combined the organic layers, dried over anhydrous Na2SO4, filtered and concentrated giving 903 mg of the desired amine.

Workup

  1. extractionExtracted the solution 3× with ethyl acetate
  2. customto remove neutral organics
  3. extractionextracted 3× with ethyl acetate
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-84a1cf48498c48e1b2c8dbf9ee811bc6
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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