반응 #42356

반응 방정식

potassium carbonate

methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate

sodium borohydride

→

title compound

tert-Butyl 3-(benzyloxy)-1-(hydroxymethyl)propylcarbamate

용매

ethanol

반응 조건

후처리

1. 1
   온도the reaction is refluxed 2 h
2. 2
   온도The solution is cooled
3. 3
   기타The ethanol is removed under reduced pressure
4. 4
   추출the aqueous solution is extracted with chloroform
5. 5
   세척The organic layer is washed with saturated sodium bicarbonate, saturated sodium sulfate
6. 6
   건조dried (magnesium sulfate)
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure

실험 절차

To an ice-cold solution of methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate (6 g, 18.6 mmol) in absolute ethanol (100 mL) is added sodium borohydride (2.8 g, 74.2 mmol), and the reaction is refluxed 2 h. The solution is cooled, excess saturated potassium carbonate added, and stirred 16 h at room temperature. The ethanol is removed under reduced pressure, and the aqueous solution is extracted with chloroform. The organic layer is washed with saturated sodium bicarbonate, saturated sodium sulfate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 296.2 [M+H]+.

출처