3-(Boc-amino)pyridine → 3-(Boc-amino)piperidine

HRID 16245

Reaction equation

HRID 16245 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:2]=1>C(O)C.[Rh]>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13])[CH2:2]1

Participants

4

Reactant 1

HCID 109323213-(Boc-amino)pyridine

Product 1

HCID 42330413-(Boc-amino)piperidine

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3-pyridinylcarbamate (2.2 g) and 5% rhodium on carbon (200 mg) in ethanol (50 mL) at 25° C. in a paar apparatus was stirred under hydrogen at 60 pounds per square inch for 24 hours, filtered through diatomaceous earth (Celite®), and concentrated. 1H NMR (300 MHz, CDCl3) δ 5.86 (b, 1H), 3.59 (b, 1H), 3.07 (dd, 1H), 2.84 (m, 1H), 2.68 (m, 1H), 2.55 (m, 1H), 2.10 (s, 1H), 1.82 (m, 1H), 1.68 (m, 1H), 1.50 (m, 1H), 1.46 (s, 9H).

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-142f87a270f6444290990de398b3284e
Source dataset
uspto-grants-2010_06
Patent number
US07737159B2

Linked notes

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