반응 #160827

반응 방정식

(4aS,5R,8S,8aR)-8-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-[(4-fluorophenyl)amino]hexahydro-2H-chromen-4a(5H)-ol

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title compound

(4aR,5R,8S,8aR)-5-[(4-fluorophenyl)amino]-8-(hydroxymethyl)hexahydro-2H-chromen-4a(5H)-ol

용매

tetrabutylammonium fluoride

반응 조건

후처리

1. 1
   기타Excess solvent was removed
2. 2
   workup.ADDITIONthe residue was diluted with CH2Cl2
3. 3
   workup.ADDITIONadded to water
4. 4
   추출extracted with CH2Cl2
5. 5
   추출The crude extract
6. 6
   건조was dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타purified on silica gel

실험 절차

Dissolved 68 mg (4aS,5R,8S,8aR)-8-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-[(4-fluorophenyl)amino]hexahydro-2H-chromen-4a(5H)-ol in 4 mL tetrabutylammonium fluoride solution (2.0 M in THF) and stirred overnight at RT. Excess solvent was removed using a rotovap, then the residue was diluted with CH2Cl2, added to water, and extracted with CH2Cl2. The crude extract was dried over Na2SO4, filtered, concentrated, then purified on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ=1.32-1.39 (m, 1H), 1.55-1.90 (m, 5H), 2.06-2.16 (m, 2H), 2.24-2.28 (m, 1H), 2.34-2.46 (m, 1H). 3.46 (s, 1H), 3.49-3.56 (m, 2H), 3.68-3.75 (m, 1H), 3.77-3.82 (m, 1H), 4.12 (dd, J1=11.4 Hz, J2=6.0 Hz, 1H), 4.64 (d, J=11.2 Hz), 6.50-6.56 (m, 2H), 6.85-6.90 (m, 2H) ppm.

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