tert-Butyl ((6-methylpyridin-2-yl)methyl)carbamate → Tert-butyl (6-methylpiperidin-2-yl)methylcarbamate

HRID 60832Notes

Reaction equation

HRID 60832 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:4][CH:3]=1.[H][H]>CO>[CH3:1][CH:2]1[NH:7][CH:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 63788697tert-Butyl ((6-methylpyridin-2-yl)methyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 62321238Tert-butyl (6-methylpiperidin-2-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nishimura catalyst (0.53 g) was added to a solution of tert-butyl (6-methylpyridin-2-yl)methylcarbamate (4.4 g, 0.02 mmol) in MeOH (60 mL) in a Parr Shaker high pressure vessel which was installed on Parr Shaker. The vessel was shaken under constant 5 bar hydrogen pressure for 30 min. The reaction mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated in vacuo to give desired product rac-tert-butyl (6-methylpiperidin-2-yl)methylcarbamate which was used for next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 3.20-3.17 (m, 1H), 3.01-2.96 (m, 1H), 2.72-2.64 (m, 2H), 1.82-1.77 (m, 1H), 1.63-1.54 (m, 2H), 1.49 (s, 9H), 1.39-1.35 (m, 2H), 1.12-0.99 (m, 5H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-90773be20f78496f910830e6ded86bd4
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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