反应详情

To a mixture of 4-methyl-4-(p-nitrobenzyloxycarbonyl)aminovaleric acid (14.0 g) and triethylamine (5.25 g) in tetrahydrofuran (280 ml), ethyl chloroformate (5.64 g) was added with ice-cooling and then stirred for 30 minutes. The resulting triethylamine hydrochloride was removed by filtration. To filtrate was added sodium borohydride (5 g) in water (90 mg) with ice-cooling, and the mixture was stirred for 1.5 hours. The reaction mixture was concentrated to a volume of 120 ml in vacuo and extracted with dichloromethane. The dichloromethane layer was washed with diluted hydrochloric acid and then water, dried over anhydrous sodium sulfate and evaporated in vacuo to give an oily residue which was then purified by silica gel chromatography to give 4-methyl-4-(p-nitrobenzyloxycarbonyl)aminopentanol.

1. additionwas added with ice-
2. temperaturecooling
3. customThe resulting triethylamine hydrochloride was removed by filtration
4. additionTo filtrate was added sodium borohydride (5 g) in water (90 mg) with ice-
5. temperaturecooling
6. stirringthe mixture was stirred for 1.5 hours
7. concentrationThe reaction mixture was concentrated to a volume of 120 ml in vacuo
8. extractionextracted with dichloromethane
9. washThe dichloromethane layer was washed with diluted hydrochloric acid
10. dry with materialwater, dried over anhydrous sodium sulfate
11. customevaporated in vacuo
12. customto give an oily residue which
13. customwas then purified by silica gel chromatography