Reaktion #160814

Reaktionsgleichung

(1aS,5aS)-hexahydro-4H-oxireno[i]isochromene

4-fluoroaniline

trimethylaluminum

→

title compound

(4aS,8R,8aR)-8-[(4-fluorophenyl)amino]hexahydro-1H-isochromen-8a(3H)-ol

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was warmed
2. 2
   Waschenrinse)
3. 3
   workup.ADDITIONwas then added
4. 4
   TemperaturThe reaction was cooled to 0° C.
5. 5
   workup.ADDITIONtreated with 50% NaOH (1 mL)
6. 6
   workup.ADDITIONwater (1 mL) The mixture was diluted with more water
7. 7
   Extraktionextracted 3× with CH2Cl2
8. 8
   TrocknenThe combined organics were dried (anhd. Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe residue was purified by column chromatography

Vorschrift

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 and stirred to rt for 30 min. (1aS,5aS)-hexahydro-4H-oxireno[i]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 6.84-6.90 (m, 2H), 6.51-6.57 (m, 2H), 3.90-3.97 (m, 1H), 3.50-3.64 (m, 3H), 3.35-3.45 (m, 2H), 2.61 (s, 1H), 1.95-2.04 (m, 1H), 1.32-1.75 (m, 8H). HRMS (ES) m/z M+H cal'd: 266.1551. found: 266.1548.

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