Sodium Methoxide → (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[NH:13][C@@H:12]([C@@H:14]([O:16]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH3:15])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[NH:13][C@@H:12]([C@@H:14]([OH:16])[CH3:15])[CH2:11][O:10][CH2:9]2)=[CH:6][CH:7]=1Participants
4
Procedure
To a solution of 4-nitrobenzoic acid (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethyl ester (1.46 g mg) in methanol (40 mL) was added sodium methoxide (1.9 mL, 28% methanol solution), and the resultant solution was stirred at room temperature for 1 hour. Solvent was removed by distillation under reduced pressure, and the resultant product was diluted with ethyl acetate and water. The organic layer was partitioned and washed with brine. The organic layer was then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/3), to thereby obtain the titled compound (833 mg). The physical properties of the compound were as follows.