Sodium Iodide → HCID 18600757, compound

Participants

Reaction Steps

36.3 g of pyridine hydrobromide perbromide are added to a solution of 16.8 g of 17,17-ethylenedioxyandrost-5-ene-3β,11β-diol in 102 ml of tetrahydrofuran and the whole is stirred at room temperature for 21/2 hours. 26.9 g of sodium iodide are added to the mixture, which is then stirred for a further 30 minutes; a solution of 36.3 g of sodium thiosulphate in 50.4 ml of water, and 100 ml of pyridine are added in succession to the mixture and stirring is continued for a further 2 hours at room temperature. The reaction mixture is diluted with 100 ml of water and concentrated under a water-jet vacuum at approximately 45°. The residue is taken up in ethyl acetate and washed in succession with saturated sodium chloride solution, ice-cold dilute hydrochloric acid, ice-cold dilute sodium hydroxide solution and again with saturated sodium chloride solution and dried over sodium sulphate. Distilling off the solvent under a water-jet vacuum results in an amorphous residue comprising crude 16α-bromo-17,17-ethylenedioxyandrost-5-ene-3β, 11β-diol. The resulting crude product (13 g) is dissolved in 143 ml of dimethyl sulphoxide, and, while stirring, a mixture of 7 g of potassium tert.-butoxide in 13 ml of dimethyl sulphoxide is added at 45° in the course of 30 minutes and stirring is continued for 20 hours at 50° (bath temperature). The mixture is cooled to room temperature, diluted with approximately 1300 ml of a saturated ammonium chloride solution and taken up in ethyl acetate; the organic phase is washed three times with saturated sodium chloride solution and dried over sodium sulphate. By distilling off the solvent under a water-jet vacuum there is obtained amorphous 17,17-ethylenedioxyandrosta-5,15-diene-3β,11β-diol of a purity adequate for further processing.

Provenance & Evidence