Potassium Cyanide → (S)-Benzyl 3-cyanopyrrolidine-1-carboxylate

HRID 2087088

Reaktionsgleichung

Reaktionsgleichung von HRID 2087088
S([C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)(C1C=CC(C)=CC=1)(=O)=O.[C-:26]#[N:27].[K+].[Cl-].[Na+].O.O>CS(C)=O>[C:26]([C@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:12]1)#[N:27]

Komponenten

5

Edukt 3

HCID 9032Potassium CyanideHCID 23713072Sodium chloride dihydrateHCID 671827093-Tosyl-Cbz-(R)-Pyrrolidine

Produkt 1

HCID 44828648(S)-Benzyl 3-cyanopyrrolidine-1-carboxylateAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Tosyl-Cbz-(R)-pyrrolidine (20.4 g, 0.05 mol) was dissolved in DMSO (54 mL), followed by the addition of KCN (5.3 g, 0.08 mol). The reaction mixture was stirred for 5 h at 80° C. The solution was cooled to room temperature and brine/H2O (90 mL) (1/1, v/v) was added. The aqueous solution was extracted with ethyl acetate. The organic extracts were dried over MgSO4, and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (1/1, v/v) to afford 8.13 g (65% yield) of the desired product as an oil.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes (1/1

Quellen und Nachweise

ORD-Eintrag
ord-82a8e1471e734796aa781be9dd8f2219
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727368B1

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