Acetic Acid → HCID 28280528, Verbindung

Reaktionsgleichung

Cl.[S:2]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1CC#N)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:20]([OH:23])(=[O:22])[CH3:21]>>[S:2]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:21][C:20]([OH:23])=[O:22])([C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Komponenten

Edukt 3

HCID 176Acetic Acid

HCID 313Hydrochloric Acid

HCID 57059856HCID 57059856, Verbindung

Produkt 1

HCID 28280528HCID 28280528, VerbindungAusbeute 48,2 %

Versuchsvorschrift

Concentrated hydrochloric acid (20 ml) was added to a solution of (2S)-2-(1-tosylpyrrolidin-2-yl) acetonitrile (4.35 g) prepared in Reference Example 50 in acetic acid (4 ml) and then the reaction solution was heated under reflux for 3 hours. After cooling the reaction solution, it was poured into ice water and then extracted with ether. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/methanol (99/1) to give 6.93 g (yield 48.2%) of the title compound.