tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate → tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

HRID 1626775Notes

Reaction equation

HRID 1626775 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2]>C(OCC)(=O)C.[Pd]>[C:1]([CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)#[N:2]

Participants

4

Reactant 1

HCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate

Product 1

HCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylateYield 112.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(cyanomethylene)piperidine-1-carboxylate (20 g, 91 mmol) was dissolved in ethyl acetate (400 mL), and 10% palladium-activated carbon (3.0 g) was added, followed by stirring at room temperature for 3.5 hours under a hydrogen atmosphere. The reaction solution was filtered with celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.38 (hexane/ethyl acetate=3/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (23 g) as a white solid (quantitative yield).

Workup

  1. filtrationThe reaction solution was filtered with celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.38 (hexane/ethyl acetate=3/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0aba60d12cc34640848f0377f15b999e
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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