Catechol → HCID 70357672, compound

Participants

Reaction Conditions

Reaction Steps

3-α-methyl-5-β-androstan-17-one was synthesized by the addition of catechol phosphochloridate (35 g, 200 mmol) and pyridine (15 g, 189.6 mmol) to 3-α-hydroxy-5-β-androstan-17-one (50.1 g, 173.0 mmol) in 1000 ml of methylene dichloride. The solution was magnetically stirred for 0.5 hour at room temperature (25° C.). Iodine (70 g, 275 mmol) was then added slowly to the solution and the stirring continued for an additional 2 hours at 25° C. The solution was washed with aqueous sodium sulfite (5%), dilute HCl, water, and dried over magnesium sulfate. It is important that the sodium sulfite solution not be saturated to prevent formation of emulsions. Approximately half of the aqueous solvent was removed under reduced pressure. Ether (2000 ml) was then added, and the entire solution passed through a short column of neutral alumina to remove colored impurities. The ether/solvent was evaporated from the column effluent under reduced pressure to yield 3α-iodo- 5β-androstan-17-one. This product was pure enough to be used in the next step without recrystallization.

Provenance & Evidence