tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate → 1-Boc-3-(aminomethyl)piperidine

HRID 896512Notes

Reaction equation

HRID 896512 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH2:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22647380tert-Butyl 3-(azidomethyl)piperidine-1-carboxylate

Product 1

HCID 27564831-Boc-3-(aminomethyl)piperidineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-azidomethylpiperidine-1-carboxylic acid tert-butyl ester (5.0 g, 20.8 mmol), ethanol (125 mL) and 10% palladium on charcoal (1.5 g) was shaken under a hydrogen atmosphere (60 psig) for 5 hours. The mixture was filtered. The filtrate was concentrated to provide a colorless oil (4.27 g, 96%) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ3.91 (b, 1H), 3.82 (dt, J=13, 4 Hz, 1H), 2.90 (m, 1H), 2.8-2.5 (m, 3H), 1.85 (m, 1H), 1.75 (s, 2H), 1.66 (m, 1H), 1.6-1.4 (m, 2H), 1.47 (s, 9H), 1.20 (m, 1H). Mass spec (AP+) m/z 215.2 (M+H+, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9545baed5c254b2cafc3c4a7c2ca9033
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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