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

HRID 1986179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986179
[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]

Komponenten

6

Edukt 2

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

Produkt 1

HCID 66660780Tert-butyl 4-(cyanomethyl)-4-methylpiperidine-1-carboxylateAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-846fb18cc1b44195a6abb937a7a8122b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547691B2

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