tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(2-methoxyphenyl)piperidine-1-carboxylate

HRID 276887Notes

Reaction equation

HRID 276887 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 22629561tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22629567Tert-butyl 4-(2-methoxyphenyl)piperidine-1-carboxylateYield 79.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1-t-Butoxycarbonyl-4-(2-methoxyphenyl)-1,2,3,6-tetrahydropyridine (150 mg, 0.52 mmol) and 10% palladium-carbon (30 mg) were stirred in methanol for two nights in an atmosphere of hydrogen. The reaction solution was filtered and the thus obtained residue was thoroughly washed with methanol. Then the filtrate and washed solution were combined and evaporated under a reduced pressure to obtain 120 mg of the aforementioned compound of interest (0.42 mmol, 81% in yield).

Workup

  1. filtrationThe reaction solution was filtered
  2. washthe thus obtained residue was thoroughly washed with methanol
  3. washThen the filtrate and washed solution
  4. customevaporated under a reduced pressure
  5. customto obtain

Sources & evidence

ORD record
ord-1c93181ed6c141e88aedf99d29168dff
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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