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

HRID 1269176Notes

Reaction equation

HRID 1269176 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[C:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH:20]=1>CCOC(C)=O.CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:19][CH2:20]1

Participants

5

Reactant 1

HCID 16756286tert-butyl 4-[2,4-difluoro-5-(isobutyrylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 16757165Tert-butyl 4-[2,4-difluoro-5-(isobutyrylamino)phenyl]-1-piperidinecarboxylateYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4-[2,4-difluoro-5-(isobutyrylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate (2.40 g, 6.31 mmol) and 10% Pd/C (500 mg) in EtOAc (40.0 mL) and MeOH (10.0 mL) was hydrogenated (200 psi) at room temperature overnight. The reaction mixture was filtered through celite and washed with ethanol (3×10 mL). The combined extracts were concentrated in vacuo to afford 2.04 g (5.34 mmol, 85%) of tert-butyl 4-[2,4-difluoro-5-(isobutyrylamino)phenyl]-1-piperidinecarboxylate: ESMS m/e: 383.2 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-a91fe027869649209b471986fe5d3245
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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