tert-Butyl 3-azidopiperidine-1-carboxylate → 1-BOC-3-Aminopiperidine

HRID 1584267Notes

Reaction equation

HRID 1584267 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[NH2:1][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

Participants

4

Reactant 1

HCID 547722tert-Butyl 3-azidopiperidine-1-carboxylate

Product 1

HCID 5458091-BOC-3-Aminopiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-azido-N-t-butoxycarbonylpiperidine (850 mg) in ethyl acetate (50 ml) was hydrogenated in the presence of 10% Pd/C (550 mg) at atmospheric pressure for 2.5 h. The reaction mixture was then filtered through Celite and the filtrate concentrated in vacuo to give the title compound. 1H NMR (CDCl3) d 1.46 (s, 9 H), 1.66-2.05 (m, 4 H), 2.57 (br s, 1 H), 2.78 (m, 4 H), 3.80 (br d, 2 H).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-6545213480014f10b07d078d49433929
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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