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

HRID 470617Notes

Reaction equation

HRID 470617 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]#[N:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]#[N:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate2×

Product 1

HCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Cyanomethylene-piperidine-1-carboxylic acid tert-butyl ester (compound of Example 14; 6.9 g, 31.0 mmol) and Pd/C (0.7 g) in ethanol (150 mL) was maintained under hydrogen atmosphere for 8 h. The reaction mixture was filtered through Celite and the solvent was evaporated to afford the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-818dcfa918dd4a16a8512cc81129a5aa
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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