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

HRID 1616075Notes

Reaction equation

HRID 1616075 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.O.[C-:21]#[N:22].[Na+]>C(O)C>[C:21]([CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)#[N:22]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Product 1

HCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (15.3 g) was dissolved in ethanol (80 mL), water (20 mL) and sodium cyanide (4.0 g, 80 mmol) were added, and stirring was conducted at 80° C. for 24 hours. Ethanol was distilled off, water and ethyl acetate were added, and then the resultant mixture was subject to Celite filtration, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by using silica gel column chromatography (hexane:ethyl acetate=3:1→2:1) to give tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (6.87 g, 77%, 3 steps) as a white solid.

Workup

  1. distillationEthanol was distilled off
  2. additionwater and ethyl acetate were added
  3. filtrationthe resultant mixture was subject to Celite filtration
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customthe obtained residue was purified

Sources & evidence

ORD record
ord-4a8eef4698b24512b037e2164243767f
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

Loading…