تفاعل #92527

معادلة التفاعل

HCl

trans-androsterone

hydrazine hydrate

potassium hydroxide

→

5α-androstan-3β-ol

المردود 82.0%

المذيبات

ethylene glycol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةby heating
2. 2
   درجة الحرارةThe solution was heated
3. 3
   درجة الحرارةto reflux at 208° C
4. 4
   درجة الحرارةthe solution was cooled at room temperature
5. 5
   استخلاصIt was extracted with CH2Cl2 (4×30 mL)
6. 6
   أخرىThe organic layer were collected
7. 7
   تجفيفdried over Na2SO4
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe resulting solid residue was recrystallized in MeOH

الإجراء التجريبي

In a flame-dried flask, potassium hydroxide (1.58 g, 28.2 mmol) was dissolved in ethylene glycol (10 mL) by heating. The solution was cooled at room temperature before adding trans-androsterone (2.00 g, 6.89 mmol) and hydrazine hydrate (0.98 mL, 20.2 mmol). The solution was heated to reflux at 208° C. After 23 h, the solution was cooled at room temperature before adding HCl (14.1 mL, 2M). It was extracted with CH2Cl2 (4×30 mL). The organic layer were collected, combined, dried over Na2SO4, and concentrated under reduced pressure. The resulting solid residue was recrystallized in MeOH to afford 5α-androstan-3β-ol (1.56 g, 82%). 1H NMR (300 MHz, CDCl3): d 3.58 (heptet, J=4.9 Hz, 1H), 1.76-1.82 (m, 1H), 1.70-1.75 (m, 2H), 1.65-1.69 (m, 2H), 1.61-1.63 (m, 1H), 1.57-1.60 (m, 1H), 1.52-1.57 (m, 2H), 1.47-1.50 (m, 1H), 1.40-1.45 (m, 1H), 1.33-1.39 (m, 1H), 1.29-1.30 (m, 1H), 1.22-1.28 (m, 4H), 1.04-1.17 (m, 4H), 0.9-1.02 (m, 1H), 0.85-0.93 (m, 2H), 0.80 (s, 3H), 0.68 (s, 3H) 0.60-0.65 (m, 1H).

المصدر