Enanthate

Norethindrone andISlorethindrone Acetate. Norethindrone (28) and its acetate or enanthate are used in oral contraceptives. 

Norethindrone may be recrystakhed from ethyl acetate (111). It is soluble in acetone, chloroform, dioxane, ethanol, and pyridine slightly soluble in ether, and insoluble in water (112,113). Its crystal stmcture has been reported (114), and extensive analytical and spectral data have been compiled (115). Norethindrone acetate can be recrystakhed from methylene chloride/hexane (111). It is soluble in acetone, chloroform, dioxane, ethanol, and ether, and insoluble in water (112). Data for identification have been reported (113). The preparation of norethindrone (28) has been described (see Fig. 5). Norethindrone acetate (80) is prepared by the acylation of norethindrone. Norethindrone esters have been described ie, norethindrone, an appropriate acid, and trifiuoroacetic anhydride have been shown to provide a wide variety of norethindrone esters including the acetate (80) and enanthate (81) (116). 

A. Heptoic anhydride enanthic anhydride). In a 250-ml. round-bottomed three-necked flask, equipped with a stirrer, dropping funnel, and thermometer, are placed 15.8 g. (16.1 ml., 0.2 mole) of dry pyridine (Note 1) and 25 ml. of dry benzene (Note 2). I hen 14.8 g. (15.5 ml., 0.1 mole) of heptoyl chloride (Note 3) is added rapidly to the stirred solution. The temperature rises only slightly, and a pyridinium complex separates. While stirring is continued, 13.0 g. (14.1 ml., 0.1 mole) of heptoic acid (Note 3) is added from the dropping funnel over a period of 5 minutes. The temperature rises rapidly to 50-65° (Note 4), and pyridine hydrochloride is formed. After stirring for 10 minutes, the solid is collected on a chilled Buchner funnel and washed twice with 25-ml. portions of dry benzene (Note 5). 

Chemical Designations - Synonyms. Enanthic alcohol 1-HeptanoI Heptyl alcohol 1-Hydroxyheptane Chemical Formula CH3(CHj)jCH20H. 

Onanth-. enanth-, oenanth-. -ather, m. enanthic (or oenanthic) ether, -sSure, /, enanthic (or oenanthic) acid, -ylsaure, /, enanthylic (or oenanthylic) acid. 

---