Tert-butyl 4-(4-cyanophenyl)-3,6-dihydropyridine-1(2h)-carboxylate → Tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate

HRID 541181Notes

Reaction equation

HRID 541181 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 1

HCID 11289112Tert-butyl 4-(4-cyanophenyl)-3,6-dihydropyridine-1(2h)-carboxylate2×

Product 1

HCID 22492960Tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Around-bottom flask, containing a solution of tert-butyl 4-(4-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (compound 1.3, 500 mg, 1.76 mmol, 1.00 equiv) in ethyl acetate (20 mL) was purged with nitrogen gas. To the solution was then added palladium on carbon (0.1 g, 10%, 60% water) and the flask was then further purged with nitrogen. The atmosphere was then changed to hydrogen and the mixture was stirred overnight at room temperature. After purging the system with nitrogen, the solids were removed by filtration and the filtrate was concentrated under reduced pressure to yield 0.2 g (40%) of the title compound as a yellow oil.

Workup

  1. customwas purged with nitrogen gas
  2. customadded palladium on carbon (0.1 g, 10%, 60% water) and the flask was then further purged with nitrogen
  3. customAfter purging the system with nitrogen
  4. customthe solids were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e715233ceeb4f438add9eabb4fa59bb
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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