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United States Patent Office Patented Oct 3,211,726 United States Patent Office Patented Oct. 12, 1965 2 3,211,726 acylates with iodine. A favorable method of preparing PROCESS FOR THE PRODUCTION OF the acylhypoiodites consists in reacting iodine with a lead 68:19-OXDO-STEROIDS tetraacylate; lead diacylates and acylhypoiodites being Albert Wettstein, Riehen, and Georg Anner, Karl Heusler, formed. Monovalent, positive iodine is also contained and Jaroslav Kalvoda, Basel, Hellmut Ueberwasser, in the compounds of iodine with other halogens, i.e. Riehen, and Jules Heer, Binningen, Switzerland, assign iodine chloride or iodine bromide. It is often an ad ors to Ciba Corporation, New York, N.Y., a corpora vantage to prepare the positive iodine used, particularly tion of Delaware No Drawing. Filed Sept. 7, 1962, Ser. No. 222,168 from the acylhypoiodites, in the manner described above Claims priority, application Switzerland, July 15, 1960, directly in the reaction solution itself. In the case of 3,133/60; Oct. 28, 1960, 12,107/60; Dec. 23, 1960, 0 starting materials which contain double bonds, the use of 4,393/.60; Apr. 5, 1961, 3,989/61; June 2, 1961, iodine compounds is particularly favorable, since iodine 6,479/61; June 13, 1961, 6,895/61; Sept. 18, 1961, does not additively combine with the double bonds. 10,803/61; Sept. 22, 1961, 11,071/61; Sept. 29, 1961, Surprisingly it was found, that also 5oz-halogeno-66 11,331/61; Jan. 9, 1962, 185/62 hydroxy-steroids, which are readily accessible from A 10 Claims. (CI. 260-239.55) steroids, can be used as starting material in the process This application is a continuation in part of our co of the present invention, although it was known that such pending application Ser. No. 122,657, filed July 10, 1961, halohydrines are easily dehydrohalogenated to form. by Albert Wettstein et al., and now abandoned. 56:66-oxido-steroids, by the action of metal salts of weak The present invention relates to a new process for the acids, such as alkali metal acetates. preperation of 63:19-oxido-steroids from 19-unsubstituted 20 The process of the present invention can be carried out, 6,3-hydroxy-steroids. for example, in the following manner: The starting mate rial is dissolved or suspended in a solvent that is inert to The process of this invention is an important step in wards oxidizing agents, for example in a hydrocarbon e.g. a novel and simple conversion of normal steroids into hexane or benzene, preferably an alicyclic hydrocarbon, 19-nor-steroids. Since a number of 19-nor-steroids, more 25 such as cyclohexane, methylcyclohexane or dimethyl especially derivatives of 19-nor-testosterone and of 19. cyclohexane or a halogenated hydrocarbon, preferably nor-progesterone, are used extensively as anabolic, a polyhalogen-lower alkane or alkene, such as carbon androgenic, gestagenic and progestational agents a new tetrachloride or hexachloro-butadiene, or mixtures of process for the production of these compounds is of great two or more of said solvents. Hereupon, a lead tetra importance. So far the 19-nor-steroids were available 30 acylate, such as lead tetraacetate, iodine and a weak base, only by a complicated sequence of reactions which involve for example calcium carbonate, are added, and the reac pyrolytic aromatization of the ring A and subsequent re tion mixture is then stirred with heating under atmos duction with an alkali metal and ammonia. An alterna pheric or superatmospheric pressure. Alternatively, the tive Synthesis uses a micro-biological hydroxylation of the reaction may be carried out in an analogous manner with 19-carbon-atom followed by elimination of the angular the use of iodine and a silver acylate, or iodine and a C-19-substituent. The yield in the hydroxylation step mercury acylate (for example the acetate) or with a com however is in most cases unsatisfactory. In both known plex formed from these reagents. The time taken by the processes the possibilities for variations in substituents in reaction depends on the temperature and/or on the sol ring B, C and D are very restricted due to the drastic vent used. When the reaction is performed with lead conditions in the pyrolysis step on one hand and to the 40 tetraacetate in boiling cyclohexane, it is in general com Substrate-specificity of the enzymatic reaction on the plete after about 4 to 3 hours. other hand. Non-polar solvents favor homolytic cleavage of the The new process however gives not only high yields of hypoiodites as compared with heterolytic cleavage which the desired end products but can be applied to a wide would lead to 6-oxo-steroids. When hypoiodous acid or variety of different steroids since oxo groups, ketalized 45 its derivatives, particularly acylhypoiodites, are used as oxo groups, esterified and etherified hydroxy groups, reagents, they are preferably used in great excess, since halogen substituents or double bonds do not interfere in these too undergo homolytic cleavage into carbon dioxide the reactions claimed. and alkyl halide. From the acetylhypoiodite formed in The new process of the present invention consists in the reaction of lead tetraacetate with iodine there is easily treating a 19-unsubstituted 66-hydroxy-steroid with com 50 formed, for example methyl iodide and carbon dioxide. pounds generating monovalent positive iodine under such For the reaction according to the present invention conditions as will bring about a homolytic cleavage of it is of advantage to work at a raised temperature, for any 6-hypoiodites formed. example between 50 and 150° C. The reaction is also The 6,3-hydroxy-steroids used as starting materials are accelerated by irradiating the reaction solution with vis reacted according to the process of the invention with 55 ible and/or ultraviolet light, i.e. light of the wave length monovalent, positive iodine, particularly a compound con between 500 and 7,000 A. It is often of advantage to taining positive iodine. Such compounds are, for exam add excess, free iodine, to the irradiated reaction solu ple N-iodo-carboxylic acid amides and imides, for exam tion. When the 6-hypoiodite formed passes over into ple N-iodo-acetamide, N-iodo-succinimide or 1:3-diiodo the 66:19-oxido compound, hydroiodic acid is liberated, 5:5-dimethylhydantoin. The use of hypoiodous acid and 60 of which the free iodine is recovered by the action of a its derivatives, for example alkylhypoiodites, such as heavy metal acylate, having an oxidizing action. There tertiary butylhypoiodite, is particularly advantageous. fore it is possible to add a small quantity of iodine only, Alkylhypoiodites may be prepared, for example from when the operation is carried out in the presence of a heavy metal oxides, such as mercuric oxide, silver oxide, heavy metal acylate, having an oxidizing action. lead oxide and the like, with iodine and alcohols. Espe 65 Usually 19-unsubstituted 66:19-oxido-steroids are the cially good yields of 6p3:19-oxido-steroids are obtained only products formed in the process of the present in when acylhypoiodites are used which may be advan vention. Depending on the reaction conditions and the tageously obtained from heavy metal acylates, for exam starting materials, there can, however, be obtained as ple acetates, propionates, trifluoracetates, benzoates of by-products, 66:19-oxido-19-hydroxy-steroids, which are the metals of the first and second sub-groups of the 70 the cyclohemiacetals of 6,3-hydroxy - 19 - oxo-steroids. Periodic Table, for example from silver and mercuric These compounds preferably can be obtained, when the 3,211,726 3. 4. system generating monovalent position iodine is formed the process claimed may belong to the androstane, preg by a lead tetraacylate and iodine and the starting ma name, cholane, cholestane, spirostane, stigmastane and terial contains in the 11-position an oxo group or a free cardanolide series. Their ring system may contain fur or esterified a-hydroxyl group. Small amounts of 19:66 ther substituents, more especially in one or several of the lactones may also be formed in some cases. positions 1 to 5, 7 to 9, 11, 12, 14 to 17 and 19 to 21, such If desired, the oxygenated 19-methyl group in a 66:19 as functionally converted hydroxyl or free or functionally oxido-steroid obtained by the present process can be fur converted oxo groups, hydrocarbon radicals, which latter ther oxidized, for example by treating the 63:19-oxido may also be attached in the 60-position, and/or halogen steroid with a strong oxidant, for example ruthenium atoms. The term "functionally converted hydroxy and tetroxide or preferably with a derivative of hexavalent oxo groups' designates esterified or etherified hydroxy chromium, such as chromic acid or tertiary butyl chro O groups or ketalized oxo groups. Compounds containing mate, in a solvent such, for example, as a lower fatty OXO groups may also be converted into enol derivatives, acid such as acetic or propionic acid, or in a chlorinated such as enol ethers or enol esters. Furthermore the new hydrocarbon such as carbon tetrachloride, more espe compounds may contain double bonds or oxido groups, cially at an elevated temperature ranging from 50 to for example in positions 4:5, 9:11 or 16:17. 100 C. In this manner, by introducing an oxo group Especially important starting materials are 66-hydroxy in position 19, there are obtained lactones of 68-hydroxy androstanes, pregnanes and -spirostanes, which contain steroid-19-oic acids. These lactones are also accessible in positions 3 and 5 substitutents which, subsequent to the by oxidation of the 19-hydroxy-63:19-oxido-compounds formation of the 66:19-oxido bridge, allow the introduc mentioned above.
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