Ethyl 4-oxoazepane-3-carboxylate hydrochloride → HCID 86754064, Verbindung
Reaktionsgleichung
[ClH:1].[O:2]=[C:3]1[CH2:9][CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H][H]>C(O)C.[Ru]>[ClH:1].[OH:2][C@@H:3]1[CH2:9][CH2:8][CH2:7][NH:6][CH2:5][C@H:4]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
As in Example 2, 23.2 g of ethyl 4-oxo-azepan-3-carboxylate hydrochloride in 90 ml of ethanol were hydrogenated with a solution of 36.1 mg of the ruthenium catalyst in 10 ml of ethanol under 40 bar hydrogen pressure at 30° C. for 21 hours and at 50° C. for 3 hours. The residue, consisting of about 80% 3R,4R and 20% 3S,4R isomers, was triturated with tetrahydrofuran and ethanol at 50° C. for half an hour and at room temperature for 4 hours. The crystals were filtered off under suction, washed with a small amount of tetrahydrofuran/ethanol and dried to constant weight at 50° C./20 mbar, to yield 13.3 g of enantiomerically pure ethyl (3R,4R)-4-hydroxy-azepan-3-carboxylate hydrochloride in the form of white crystals.