تفاعل #160827

معادلة التفاعل

(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

المذيبات

tetrabutylammonium fluoride

ظروف التفاعل

المعالجة

1. 1
   أخرىExcess solvent was removed
2. 2
   workup.ADDITIONthe residue was diluted with CH2Cl2
3. 3
   workup.ADDITIONadded to water
4. 4
   استخلاصextracted with CH2Cl2
5. 5
   استخلاصThe crude extract
6. 6
   تجفيفwas dried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىpurified on silica gel

الإجراء التجريبي

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.

المصدر