6-Dehydro-17-methyltestosterone

Alternatively, as described in U.S. Patent 3,341,557, 6-dehydro-17-methyltestosterone may be used as the starting material. A mixture of 0.4 g of cuprous chloride, 20 ml of 4 M methylmagnesium bromide in ether and 60 ml of redistilled tetrahydrofuran was stirred and cooled in an ice bath during the addition of a mixture of 2.0 g of 6-dehydro-l 7-methyl-testosterone, 60 ml of redistilled tetrahydrofuran and 0.2 g of cuprous chloride. The ice bath was removed and stirring was continued for four hours. Ice and water were then carefully added, the solution acidified with 3N hydrochloric acid and extracted several times with ether. The combined ether extracts were washed with a brine-sodium carbonate solution, brine and then dried over anhydrous magnesium sulfate, filtered and then poured over a 75-g column of magnesium silicate (Florisil) packed wet with hexanes (Skellysolve B). The column was eluted with 250 ml of hexanes, 0.5 liter of 2% acetone, two liters of 4% acetone and 3.5 liters of 6% acetone in hexanes. 

Penicillin G hydrabamine Dehydroabietyl ethylene diamine Penicillin V hydrabamine 1 -Dehydro-6tt-methyl-9a-fluorohydro-cortisone Fluorometholone 6-Dehydro-17-methyltestosterone Calusterone... 

Dehydrotestosterone Derivatives. Irradiation of 1-dehydro-4-methyltestosterone acetate (Formula 57, R=H) in dioxane gives Formula 58 (R=H), an analog of lumisantonin, in 60-70% yield (37). 

Figure 18-2. Separation of hormones on ChromSpher UOP colnmn at 30°C at different eluent inlet temperatnres a, 5°C b, 10°C c, 22°C d, 30°C. Componnds 1, thiourea 2, hydrocortisone 3, nortestosterone 4, dehydro-17a-methyltestosterone 5, testosterone 6,17a-methyItestosterone. (Reprinted from reference 12, with permission from Elsevier.)...

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