반응 #1758077

반응 방정식

(1S)-2,3-dibromo-bicyclo[3.2.0]heptan-6-one

[9-(tert-butyl-dimethyl-silanyloxy)-nonyl]-methyl-amine

→

(1S,4S,7S)-5-Bromo-7-{[9-(tert-butyl-dimethyl-silanyloxy)-nonyl]-methyl-amino}-bicyclo[2.2.1]heptan-2-one

용매

acetone

반응 조건

후처리

1. 1
   기타After evaporation of the solvent the residue
2. 2
   세척washed with a satd NaHCO3 (aq)/brine mixture
3. 3
   추출The aqueous layer was extracted with diethyl ether
4. 4
   건조The combined organic layers were dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated to dryness
7. 7
   기타to afford a dark brown oil, which
8. 8
   기타was purified by column chromatography over silica gel using a gradient of 5-15% diethyl ether/pentane as eluent
9. 9
   기타After evaporation of the volatiles the title compound
10. 10
    기타was obtained as a light yellow/brown oil

실험 절차

To a solution of (1S)-2,3-dibromo-bicyclo[3.2.0]heptan-6-one (2.15 g, 8.02 mmol) in acetone (20 mL) was added [9-(tert-butyl-dimethyl-silanyloxy)-nonyl]-methyl-amine (5.77 g, 12.3 mmol) and the reaction mixture was stirred at RT for 3 days. After evaporation of the solvent the residue was taken up in diethyl ether/ethyl acetate and washed with a satd NaHCO3 (aq)/brine mixture. The aqueous layer was extracted with diethyl ether. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness to afford a dark brown oil, which was purified by column chromatography over silica gel using a gradient of 5-15% diethyl ether/pentane as eluent. After evaporation of the volatiles the title compound was obtained as a light yellow/brown oil.

출처