Citric Acid → 3alpha-Hydroxy-21-morpholino-5alpha-pregnane-11,20-dione citrate

Participants

Reaction Steps

A solution of 3α-hydroxy-21-morpholino-5α-pregnane-11,20-dione (83.52 mg. 0.2 mmole) in absolute ethanol (1 ml.) was treated with 0.1M aqueous citric acid (2 ml. 0.2 mmole). The ethanol was removed by evaporation and the resulting solution freeze-dried. Water (5 ml.) was added, and the cloudy solution obtained left to stand at room temperature for two hours. The solution was filtered through a No. 3 sinter. The flask was rinsed with water (0.5 ml.) and this was also filtered. The sinter and flask were washed with chloroform (10 ml.). The chloroform was washed with saturated sodium bicarbonate solution (2 × 5 ml.) and with water (3 × 5 ml.) and evaporated to a residue which was dried by azeotroping with benzene (6 × 10 ml.) and in vacuo (20.6 mg.). The filtrate waas diluted with water (1 ml.) to give title compound as a 10 mg./ml. aqueous solution with respect to steroid. The pH of the solution was 3.45.

Provenance & Evidence