反应详情

Potasium tert-butoxide (7.6 g, 67.8 mM) and (20S)-20-hydroxymethylpregn-4-en-3-one (6.6 g, 20 mM) are combined in tert-butanol and heated at reflux temperature for 120 minutes. 2-ethylhexylnitrate (3.56 ml, 20 mM) is then added in one continuous portion. After 10 minutes, the reaction vessel is cooled to room temperature. The reaction is then quenched with acetic acid (9 ml) and stirred overnight. After diluting with dichloromethane (200 mL), the solids are removed, washed, and combined with the washing residue and subsequently purified as described in Example 1 to give crystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one.

1. temperatureheated
2. temperatureat reflux temperature for 120 minutes
3. customThe reaction is then quenched with acetic acid (9 ml)
4. additionAfter diluting with dichloromethane (200 mL)
5. customthe solids are removed
6. washwashed
7. customsubsequently purified
8. customto give
9. customcrystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one