반응 #65319

반응 방정식

N-Boc-O-benzylserine methyl ester

diisobutylaluminium hydride

Hydrochloric acid

→

N-Boc-O-benzylserinal

용매

toluene

toluene

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for an additional 20 minutes
2. 2
   기타to reach -50° C
3. 3
   기타the resulting reaction mixture
4. 4
   기타to reach -10° C
5. 5
   기타The organic layer was separated
6. 6
   추출the aqueous layer was extracted with ethylacetate (2×100 ml)
7. 7
   건조The combined organic solution was dried with sodium sulphate
8. 8
   기타evaporated to dryness below 40° C. (bath temperature)

실험 절차

N-Boc-O-benzylserine methyl ester (9.5 g, 32 mmol) was dissolved in dry toluene (distilled from sodium) (100 ml). The solution was cooled to -70° C., and a solution of diisobutylaluminium hydride in toluene (1.2M, 53 ml, 64 mmol) was added dropwise over a period of 45 minutes under vigorous stirring under nitrogen. The mixture was stirred for an additional 20 minutes and was then allowed to reach -50° C. Hydrochloric acid (2M, 150 ml) was carefully added and the resulting reaction mixture was allowed to reach -10° C. The organic layer was separated and the aqueous layer was extracted with ethylacetate (2×100 ml). The combined organic solution was dried with sodium sulphate and evaporated to dryness below 40° C. (bath temperature). The N-Boc-O-benzylserinal was isolated as a colourless oil. Yield 8.6 g (96%). The structure was confirmed by 1HNMR and 13CNMR.

출처