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• Synthesis

  trestolone acetate was prepared as follows:

  Tetrahydrofuran (717.6 g), compound (5A) (204 g), and anhydrous copper acetate (II) (23.6 g) were placed in a suitable container. The slurry was stirred and cooled to between -45°C and -35°C. Then, methylmagnesium chloride solution (23%, dissolved in THF, analytical concentration 22.6%, 346.1 g) was slowly added at a rate that maintained the reaction temperature between -45°C and -35°C for a minimum of 3 hours. After the addition was complete, the reaction mixture was stirred between -45°C and -35°C and monitored by HPLC. Then, the mixture was finished with 37% hydrochloric acid (128.1 g), maintaining the temperature below 10°C. The mixture was maintained below 10°C for 30 minutes. During approximately 20 minutes, water (408 g) was slowly added. Heptane (428.2 g) was added and the mixture was heated to room temperature. The aqueous phase was separated and the product was extracted with heptane.

  The combined organic extract was washed with 25% ammonium hydroxide solution and purified water. The solvent was distilled at atmospheric pressure until approximately 3 volumes remained [relative to the feed amount of compound (5A)]. Tert-butyl methyl ether was added and the mixture was cooled to crystallize the product trestolone acetate. The product was separated by filtration and dried at 40–50 °C (yield: 78%; alpha:beta ratio = 99).;

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