tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate → Tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]1-piperidinecarboxylate

HRID 1832263Notes

Reaction equation

HRID 1832263 reaction equation
[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([C:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=2)[CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[H][H]>CCO.[Pd]>[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:17][CH2:18]2)[CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 16756287tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 16756289Tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]1-piperidinecarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate (335 mg, 0.93 mmol) and 10% Pd/C (35.0 mg) in EtOH (20.0 mL) was hydrogenated at room temperature overnight using the hydrogen balloon method. The reaction mixture was filtered through celite and washed with ethanol (3×10 mL). The combined extracts were concentrated in vacuo to afford tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinecarboxylate (335 mg, 100%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with ethanol (3×10 mL)
  3. concentrationThe combined extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-311d5bfba83246ec8596809e63e1d0e6
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

Loading…