반응 #84683

반응 방정식

(1S,2S,3S,5S)-2-(tert-butyldimethylsilyloxy)bicyclo[3.1.0]hexane-3-carboxylic acid

triethylamine

benzyl alcohol

diphenyl phosphoryl azide

→

title compound

수율 54.0%

benzyl (1S,2S,3S,5S)-2-(tert-butyldimethylsilyloxy)bicyclo[3.1.0]hexan-3-ylcarbamate

수율 54.0%

용매

ethyl acetate

toluene

반응 조건

후처리

1. 1
   온도The reaction solution was cooled to room temperature
2. 2
   세척washed with water (3×50 mL) and brine (50 mL)
3. 3
   건조The organic layer was dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타to afford a crude product, which
7. 7
   기타was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:8)

실험 절차

To a solution of (1S,2S,3S,5S)-2-(tert-butyldimethylsilyloxy)bicyclo[3.1.0]hexane-3-carboxylic acid (4 g, 15.625 mmol), triethylamine (22 mL, 156 mmol) and benzyl alcohol (17 mL, 156 mmol) in toluene (50 mL) at room temperature was added diphenyl phosphoryl azide (33.7 mL, 156 mmol) dropwise, and the resulting mixture was stirred at 100° C. overnight. The reaction solution was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with water (3×50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford a crude product, which was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:8) to afford the title compound (3.0 g, 54%) as a white solid. MS (ES+) C20H31NO3Si requires: 361, found: 362 [M+H]+.

출처