Notes 5117941. Some Xteroid Hydantoins By R. J. W. CREMLYN and (MRs.) MARY CHISHOLM A WIDE range of 5-substituted hydantoins show anticonvulsant activity,l including several 5,5-spirohydantoins like 1,2,3,4-tetrahydronaphthalene-2-spiro-5'-hydantoin (tetrantoin) .2 We therefore attempted the preparation of some steroid spiro-5'-hydantoins in the hope that these might have useful biological properties. Also, the chemistry has some interesting features, since it has been recently demonstrated, 39 that substituted alicyclic ketones yield predominantly different stereoisomeric hydantoins depending on the method of preparation, and by alkaline hydrolysis these are converted into the corresponding isomeric amino-acids5 For simple substituted cyclohexane amino-acids Munday has assigned configurations to the Strecker and hydantoin products based on the resistance of l-amino-4-t-butylcyclohexanenitrile hydrochloride to hydrolysis, the infrared spectra, and dissociation constants of the amino-acids. By analogy, it was hoped to carry out a similar sequence of reactions in the steroid field, as shown, from cholestanone (I) : I 0 a9 Reagents: 1, KCN-(NH,),CO,; 2, KCN-NH,CI; 3, NaCNO-H+; 4, OH-; 5, H+ It was hoped, by investigation of the stereochemical course of the nitrous acid deamination of compounds ( 111) and (V), to confirm the conformation of the amino-group 6>7 and hence the configuration of the parent hydantoins ( 11) and (VI). We started by examining the application of the Bucherer hydantoin synthesis to some steroid ketones, beginning with cholestanone, because here the keto-group is in a relatively unhindered position. Cholestanol has been prepared by pressure hydrogenation of cholesterol under various conditi~ns.~-ll The poor results obtained at ordinary temperature and pressure appeared to be due to the low solubility of cholesterol in the solvents used. We therefore investigated hydrogenation in dioxan, cellosolve, and tetrahydrofuran. The first two were unsatisfactory, but the last-named, in the presence of perchloric acid, gave a 90% yield of cholestanol. This is an improvement over existing methods, as it does not require either