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

HRID 643562Notes

Reaction equation

HRID 643562 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 51356836tert-butyl 4-(3-cyanophenyl)-3,6-dihydropyridine-1(2H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59261051Tert-butyl 4-(3-cyanophenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-(3-cyanophenyl)-3,6-dihydropyridine-1(2H)-carboxylate (1.00 g, 3.52 mmol) was combined with 20% Pd(OH)2/C (1 g) in 25 mL of methanol. This mixture was stirred under a hydrogen atmosphere using a hydrogen filled balloon for 5 h. The reaction mixture was filtered through a celite plug and the filtrate was concentrated. Purification by MPLC (silica, 38% ethyl acetate/hexanes) gave tert-butyl 4-(3-cyanophenyl)piperidine-1-carboxylate. ESI-MS calc. for C17H22N2O2: 286; Found: 309 (M+Na+).

Workup

  1. customfor 5 h
  2. filtrationThe reaction mixture was filtered through a celite plug
  3. concentrationthe filtrate was concentrated
  4. customPurification by MPLC (silica, 38% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-65dd06ae8dbd43c386a29133bc3d4910
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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