Reaktion #160803

Reaktionsgleichung

NaOH

trimethylaluminum

4-Fluoroaniline

Trans hexahydro-1aH,4aH-oxireno[d]chromene

→

title compound

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

Lösungsmittel

water

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at rt overnight
2. 2
   TemperaturThe reaction was cooled to 0° C.
3. 3
   ExtraktionThe reaction mixture was extracted 3× with CH2Cl2
4. 4
   SonstigeThe combined organics were dried
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by column chromatography

Vorschrift

To a mixture of 4-Fluoroaniline (0.173 g, 1.56 mmol) in CH2Cl2 (3 mL) at 0° C. was added trimethylaluminum (2M in toluene, 0.778 mL) dropwise. The mixture was warmed to rt and stirred for 30 min. Trans hexahydro-1aH,4aH-oxireno[d]chromene (0.200 g, 1.30 mmol) in CH2Cl2 (2 mL) 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 reaction mixture was extracted 3× with CH2Cl2. The combined organics were dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 6.90 (t, 2H, J=8.8 Hz), 6.60 (dd, 2H, J=4.2 Hz, 8.8 Hz), 3.88 (dd, 1H, J=5.4 Hz, 12.0 Hz), 3.68-3.74 (m, 1H), 3.47 (dd, 1H, J=4.8 Hz, 11.5 Hz), 3.40 (t, 1H, J=3.2 Hz), 2.30-2.40 (m, 1H), 1.69-1.78 (m, 2H), 1.54-1.68 (m, 5H), 1.45-1.48 (m, 1H), 1.20-1.30 (m, 1H), HRMS (ES) m/z M+H calc'd.: 266.1551. found: 266.1556

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