CC(=NO)C(C)=NO.[BH4-].[Na+].[Cl:11][C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH:15]=[C:16]1[S:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].C(O)(=O)C>O.[OH-].[Na+].C1COCC1.CN(C=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:15][CH:16]1[S:20][C:19](=[O:21])[NH:18][C:17]1=[O:22]To the suspension containing CoCl2.6H2O (3.98 mg, 0.014 mmol) and dimethylglyoxime (66.13 mg, 0.57 mmol) in 10 ml of water, 4 drops of 1.0N NaOH and NaBH4 (370.06 mg, 9.62 mmol) were subsequently added. The mixture was cooled to 0° C., and 5-(3-chloro-4-(cyclohexylmethoxy)benzylidene)thiazolidine-2,4-dione (1 g, 2.83 mmol) in 15 ml of THF-DMF (2:1) was added thereto over 20 minutes. The mixture was stirred at room temperature for 18 hours, to which acetic acid was then added until the pH thereof reached about 6. The mixture was diluted with water and extracted with ethyl acetate and water. The organic layer was washed with water several times, dried with anhydrous magnesium sulfate, filtered and solvent-evaporated. The residual oil was chromatographed on silica gel to afford 5-(3-chloro-4-(cyclohexylmethoxy)benzyl)thiazolidine-2,4-dione (Derivative 117 of the above formula) as white solid (0.8 g, yield: 79%).
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