3-(Boc-amino)pyridine → 3-(Boc-amino)piperidine
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationfiltered through diatomaceous earth (Celite®)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-142f87a270f6444290990de398b3284e
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737159B2
Reaction notes
Loading…