Reacción #92530

Ecuación de reacción

NaOH

3α-Azidocholest-5-ene

Lithium aluminum hydride

water

water

→

3α-Aminocholest-5-ene

Rendimiento 93.0%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for another five minutes
2. 2
   workup.STIRRINGThe reaction was then stirred until all the salts
3. 3
   FiltraciónImmediately afterwards, the reaction was filtered
4. 4
   Secadodried (Na2SO4)
5. 5
   Concentraciónconcentrated

Procedimiento

3α-Azidocholest-5-ene (4.62 mmol, 1.9 g) was dissolved in 154 mL of anhydrous diethyl ether. Lithium aluminum hydride (46.2 mmol, 1.75 g) was then added in one portion. After 30 hours, the reaction mixture was cooled to 0° C. 1.75 mL of deionized water was then added dropwise. After stirring for five minutes, 1.75 mL of 15% aqueous NaOH was added dropwise. After stirring for another five minutes, 5.25 mL of deionized water was added dropwise. The reaction was then stirred until all the salts turned white. Immediately afterwards, the reaction was filtered, dried (Na2SO4), and concentrated to afford 3α-Aminocholest-5-ene (1.57 g, 93%) as a white solid. mp 104-106° C.; IR (thin film) 3367, 3343, 2931, 1557 cm−1; 1H NMR (300 MHz, CDCl3) d 5.37-5.34 (m, 1H), 3.15 (t, 1H, J=3.2 Hz), 2.61-2.54 (m, 1H), 2.04-1.74 (m, 6H), 1.63-1.03 (m, 21H), 1.00 (s, 3H), 0.91 (d, 3H, J=6.5 Hz), 0.86 (d, 6H, J=6.6 Hz), 0.67 (s, 3H).

Fuente