Sodium Methoxide → (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanol
Reaktionsgleichung
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[NH:16][C@@H:15]([C@@H:17]([O:19]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH3:18])[CH2:14][O:13][CH2:12]2)=[CH:7][CH:6]=1>CO>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[NH:16][C@@H:15]([C@@H:17]([OH:19])[CH3:18])[CH2:14][O:13][CH2:12]2)=[CH:9][CH:10]=1Komponenten
4
Versuchsvorschrift
Sodium methoxide (1.9 mL, 28% methanol solution) was added to a methanol (40 mL) solution of 4-nitrobenzoic acid (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholin-3 yl]ethyl ester (1.46 g). Stirring was continued for 1 hour at room temperature. The solvent was removed under a vacuum, and ethyl acetate and water were added, and the organic layer was partitioned. The organic layer was washed with brine, and the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/3), and the title compound (833 mg) was obtained. The physical property values are as follows.