Phosphorus oxychloride → Benzyl 2-cyanopyrrolidine-1-carboxylate

HRID 1170509

Reaktionsgleichung

[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=O)[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]#[N:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

Carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester (25.0 g, 101 mmol) was dissolved in pyridine (125 mL) under an N2 atmosphere and cooled to −10° C. The phosphorus oxychloride (12.6 mL, 135 mmol) was dissolved in DCM (25 mL) and added dropwise over 40 mins to the pyridine solution. The reaction mixture's temperature was maintained at −10° C. and the solution was allowed to stir for 2 hours. The reaction was quenched by addition of water/ice (100 g) and transferred into a separatory funnel. The solution was extracted with diethyl ether (3×200 mL). The organic layers were combined and washed with saturated cupric sulfate (200 mL). The organic layer was dried over MgSO4 and concentrated under vacuo to afford 20.0 g (82%) of 2-cyano-pyrrolidine-1-carboxylic acid benzyl ester as a green oil.

Aufarbeitung

temperatureThe reaction mixture's temperature was maintained at −10° C.
customThe reaction was quenched by addition of water/ice (100 g)
customtransferred into a separatory funnel
extractionThe solution was extracted with diethyl ether (3×200 mL)
washwashed with saturated cupric sulfate (200 mL)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under vacuo

Quellen und Nachweise

ORD-Eintrag: ord-677d1d6e611c477cbf27686a534e4692
Quelldatensatz: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07825256B2

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