反应详情

2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile (free form of #88) (120 mg, 0.35 mmol) was dissolved in methanol (2.4 ml) and dichloromethane (0.8 ml), then at 0° C., sodium borohydride (18 mg, 0.43 mmol) was added, followed by stirring at the same temperature for 1 hour. Next, at the same temperature, sodium borohydride (9 mg, 0.22 mmol) was further added, followed by stirring at the same temperature for 1 hour. An aqueous saturated sodium hydrogencarbonate solution was added, followed by farmer stirring for 5 minutes. The solution was extracted three times with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (91 mg) as a roughly-purified product. This was washed with isopropyl ether to obtain the entitled compound (85 mg, 70%) as a white solid.

1. stirringby stirring at the same temperature for 1 hour
2. stirringstirring for 5 minutes
3. extractionThe solution was extracted three times with chloroform
4. washwashed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe insoluble matter was separated by filtration
7. customthe solvent was evaporated away
8. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)