반응 #84681

반응 방정식

water

(R)-4-benzyl-3-((1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hexane-3-carbonyl)oxazolidin-2-one

2,6-lutidine

tert-butyldimethylsilyl trifluoromethanesulfonate

→

title compound

수율 86.0%

(R)-4-benzyl-3-((1S,2S,3S,5S)-2-(tert-butyldimethylsilyloxy)-bicyclo[3.1.0]hexane-3-carbonyl)oxazolidin-2-one

수율 86.0%

용매

dichloromethane

methanol

반응 조건

후처리

1. 1
   workup.WAITroom temperature for 1 hour
2. 2
   추출extracted with ether (2×400 mL)
3. 3
   세척The combined ether extracts were washed with brine
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:8)

실험 절차

To a stirred solution of (R)-4-benzyl-3-((1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hexane-3-carbonyl)oxazolidin-2-one (25 g, 83 mmol) and 2,6-lutidine (38.2 mL, 332 mmol) in dichloromethane (300 mL) was added tert-butyldimethylsilyl trifluoromethanesulfonate (47.6 mL, 207.5 mmol) at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. for 30 minutes and then room temperature for 1 hour. After diluted with methanol (25 mL), the mixture was poured into water and extracted with ether (2×400 mL). The combined ether extracts were washed with brine, dried over sodium sulfate, filtered, concentrated and purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:8) to afford the title compound (29 g, 86%) as a colorless oil. MS (ES+) C23H33NO4Si requires: 415, found: 416 [M+H−H2O]+.

출처