Potassium Cyanide → Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylate

HRID 1986179Notes

Reaction equation

HRID 1986179 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15]OS(C)(=O)=O)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:21]#[N:22].[K+]>CS(C)=O.CCOC(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:21]#[N:22])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 222480521-(Tert-butoxycarbonyl)-4-methyl-4-(methanesulfonyloxymethyl)piperidine

Product 1

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylateYield 77.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To 4-methanesulfonyloxymethyl-4-methylpiperidine-1-carboxylic acid tert-butyl ester (0.440 g, 1.43 mmol) dissolved in DMSO (3 mL) is added potassium cyanide (0.373 g, 5.73 mmol). The mixture is heated to 130° C. for 18 hours. The reaction mixture is cooled and diluted with EtOAc and water. The organic layer is concentrated, taken up in MeOH and concentrated again to give the title compound as a brown oil (263 mg, 77% yield).

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationThe organic layer is concentrated
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-846fb18cc1b44195a6abb937a7a8122b
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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