Réaction #160809

Équation de réaction

trans octahydrooxireno[d]isochromene

4-fluoroaniline

trimethylaluminum

→

title compound

(4R,4aR,8aR)-4-[(4-fluorophenyl)amino]octahydro-4-aH-isochromen-4a-ol

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Lavagerinse)
2. 2
   workup.ADDITIONwas then added
3. 3
   TempératureThe reaction was cooled to 0° C.
4. 4
   workup.ADDITIONtreated with 50% NaOH (1 mL)
5. 5
   workup.ADDITIONThe mixture was diluted with more water
6. 6
   Extractionextracted 3× with CH2Cl2
7. 7
   SéchageThe combined organics were dried (anhd. Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated
10. 10
    AutreThe residue was purified by column chromatography

Mode opératoire

To a mixture of 4-fluoroaniline (0.721 g, 6.48 mmol) in CH2Cl2 (6 mL) at 0° C. was added trimethylaluminum (2M in toluene, 3.24 mL) dropwise. The mixture was warmed to rt for 30 min. A mixture of both cis and trans octahydrooxireno[d]isochromene (0.200 g, 1.30 mmol) in CH2Cl2 2 mL+0.5 mL rinse) was then added and the mixture was stirred at rt overnight. The reaction was cooled to 0° C. and treated with 50% NaOH (1 mL) then water (1 mL). The mixture was diluted with more water and extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 6.94 (1, 2H, J=8.6 Hz), 6.78 (dd, 2H, J=4.2 Hz, 8.8 Hz), 4.14 (dd, 1H, J=1.5 Hz, 12.0 Hz), 3.64 (d, 1H, J=11.5 Hz), 3.56 (dd, 1H, J=4.6 Hz, 11.0), 3.48 (t, 1H, J=11.5 Hz), 3.10 (s, 1H), 1.17-2.00 (m, 9H). HRMS (ES) m/z M+H calc'd.: 266.1551. found: 266.1554

Source