tert-butyl 4-[4-fluoro-3-(methoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate → HCID 57880551, compound

HRID 643555Notes

Reaction equation

HRID 643555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)=[CH:4][C:3]=1[C:21]([O:23][CH3:24])=[O:22].[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 2

HCID 57880514tert-butyl 4-[4-fluoro-3-(methoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57880551HCID 57880551, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-[4-fluoro-3-(methoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate (2.11 g, 6.29 mmol) and 10% Pd/C (525 mg) in ethanol (60 mL) was stirred under an hydrogen atmosphere using a hydrogen filled balloon for 6 h. The reaction mixture was filtered and the filtrate was concentrated. 1H NMR analysis revealed that approximately 5% of the starting olefin remained, so the mixture was resubmitted to the above conditions for 4 h. Filtration, and concentration of the filtrate gave tert-butyl 4-[4-fluoro-3-(methoxycarbonyl)phenyl]piperidine-1-carboxylate which was used without further purification. 1H NMR (500 MHz, CDCl3) δ 7.78 (dd, J=6.5, 2.0 Hz, 1H), 7.37 (m, 1H), 7.10 (dd, J=10.5, 8.0 Hz, 1H), 4.27 (br m, 2H), 3.95 (s, 3H), 2.82 (br m, 2H), 2.69 (tt, J=12.5, 3.5 Hz, 1H), 1.83 (br d, J=13 Hz, 2H), 1.62 (dq, J=4.5, 13 Hz, 2H), 1.50 (s, 9H).

Workup

  1. customfor 6 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. filtrationFiltration, and concentration of the filtrate

Sources & evidence

ORD record
ord-cac8fd09dcac4d7094dee1b1fc78ac7f
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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