tert-Butyl (pyridin-3-ylmethyl)carbamate → tert-butyl N-[(piperidin-3-yl)methyl]carbamate

HRID 16246Notes

Reaction equation

HRID 16246 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:2]=1>C(O)C.[Rh]>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:2]1

Participants

4

Reactant 1

HCID 13948280tert-Butyl (pyridin-3-ylmethyl)carbamate

Product 1

HCID 2756030tert-butyl N-[(piperidin-3-yl)methyl]carbamate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3-pyridinylmethylcarbamate (4.3 g) and 5% rhodium on carbon (400 mg) in ethanol (50 mL) at 25° C. in a paar apparatus was stirred under hydrogen at 60 pounds per square inch for 27 hours, filtered through diatomaceous earth (Celite®), and concentrated. 1H NMR (300 MHz, CDCl3) δ 4.55 (b, 1H), 2.99 (m, 4H), 2.56 (t, 1H), 2.33 (t, 1H), 1.74 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-768044a1ab7e49fcbb115dd49f558187
Source dataset
uspto-grants-2010_06
Patent number
US07737159B2

Reaction notes

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