3  3,716,528  4  H  (X)  (IX)  (wherein R is a  hydrogen atom or  a lower alkyl group,  e.g. methyl, ethyl,  propyl, butyl; R’  and R" are the same  or different and  each is a •hydrogen  atom or a lower  alkoxy group, e.g.  methoxy, ethoxy,  propoxy;  X  is an  organic acid residue,  e.g.  p-toluenesulfonyl  group; and  Y  is a lower alkyl group,  e.g. methyl, ethyl,  propyl)  The starting compounds  (I)  are novel ones and  may  be prepared by  reacting a  3-cyclohexene-1-methylamine  (XI)  with lead tetraacetate.  In the latter stage  of the first step,  the resulting ester  derivatives are hydrolyzed  according to the  conventional  procedure of hydrolysis  of an organic acid  ester with an  alkali, e.g. an alkali  metal hydroxide  such as sodium hy› droxide, potassium  hydroxide, or  a  carbonate such  as  sodium carbonate,  sodium bicarbonate,  potassium carbon› ate, potassium  bicarbonate.  In the second step,  the resulting compounds  (III) are  oxidized to the corresponding  ketones (IV). The  oxida› tion may be achieved  by applying the  oxidizing method  or reagent for converting  secondary alcohols  to ketones  such as  N-bromosuccinimide,  Oppenauer method,  dimeth› ylsulfoxide-acetic  anhydride,  dimethylsulfoxide-dicyclo› hexylcarbodiimide  (DCC), or the like.  In the third step,  the resulting compounds  (IV) are sub› jected to  intramolecular cyclization  together with acyla› tion by interacting  an organic acid. In  this case, the reac› tion proceeds  stereospecifically  and smoothly and  affords  In the fifth step,  the lactam ring in  the resulting ether  derivatives (VI)  is reduced with  a metal hydride.  The  complex metal  hydrides used in  this step are lithium  alu› minum hydride,  lithium diethoxy  aluminum hydride,  lithium triethoxy  aluminum hydride,  lithium tri-t-butoxy  aluminum hydride,  lithium borohydride,  or the like. In  general the reduction  of lactam with metal  hydride, e.g.  lithium aluminum  hydride, directly  affords a desoxy deriv› ative  (corresponding  to the  compound VIII),  however, in  this reaction affords  intermediately  a carbinol amine,  which is farther  dehydrated  to a vinyl amine  (if neces› sary with alumina  or  phosphorus  oxychloride-pyridine;  on  the contrary,  the reduction with  an aluminum hydride,  e.g.  In the fourth step,  the XO-group in  the compounds  (V)  is displaced by the  YO-group by  a lower alcohol.  The  solvolysis is carried  out by reacting  the compound (V)  with a lower  alcohol in the presence  of an acid catalyst  such as a mineral  acid, e.g. hydrochloric  acid, sulfuric  acid, or an organic  acid, e.g.  p-toluenesulfonic  acid, or a  base catalyst such  as an alkali metal  hydroxide, e.g. sodi› um hydroxide, potassium  hydroxide,  a metal alkoxide,  e.g.  sodium  methoxide, potassium  methoxide, sodium  eth› oxide, potassium  ethoxide, potassium  t-butoxide, or  a  complex metal hydride,  e.g. sodium  borohydride, potas› sium boroliydride,  at a  temperature ranging  from room  temperature  to the refluxing  temperature  of the reaction  medium for several  hours or several days.  Lower alkanols  used in the solvolysis  are methanol, ethanol,  propanol, or  the like. In order  to avoid the side  reaction such as isom› erization; the reaction  is  preferably carried  out in basic  medium at low temperature  as mildly as possible.  In  this  case, the lower  alkyl group Y arising  from the alcohol  used ( or alkoxy  group when used  alkoxide) is introduced  into the compounds  (VI).  the objective cyclic  ester derivatives  (V) in good yield.  The reaction  is carried out at  an optional  temperature,  ranging from room  temperature  to the refluxing tempera› ture of the reaction  medium, and completed  within sev› eral minutes to several  hours. As solvent,  as far as unaf› fecting the main  reaction, the optional  solvents may be  used, and  particularly aprotic  solvents such as  hydrocar› bon solvents, e.g.  benzene, toluene,  ether solvents, e.g.  diethyl ether,  tetrahydrofuran,  dioxane, or acetonitrile,  or  protic solvents such  as acetic acid, may  be used. As or› ganic acid, most  acids, not accompanied  by steric hin› drance by bulky  group; may be used,  and in general the  acids having the  small pKa value  are more preferable.  In  view of this point  sulfonic acids, e.g.  p-toluenesulfonic  acid,  methanesulfonic  acid,  bromobenzenesulfonic  acid,  are the most  advantageous.  In  this reaction the  acid resi- due X arising  from the acid used  is  introduced into the  compounds  (V).  The :first step consists  of two stages and  the former  stage is carried out  by reacting a compound  CI) with a  compound (H),  if necessary, in  a suitable amount  of  anhydrous organic  solvent to ,give an  ester intermediate  of the compound  (III).. As organic  solvent, inert solvents  inactive to the reactive  compounds,  i.e. the compound  (:[)  and the compound  (II), for example,  an alcohol (e.g.  methanol, ethanol),  t-butanol, an ether  (e.g. diethyl ether,  tetrahydrofuran,  dioxane, diglyme),  a ketone ( e.g. ace› tone, methyl ethyl  ketone), an amine  (e.g. pyridine, pico› line ),  dimethylsulfoxide,  N,N-dimethylformarnide,  ace› tonitrile,  dichloromethane,  chloroform,  or the like, may  optionally be used.  The reaction proceeds  readily without  specially heating,  and may be carried  out in the wide range  of  temperature, such  as the ice-cooling  temperature  to  the refluxing  temperature  of the reaction medium.  The  reaction period is  about one hour or  a few days, which  may be varied according  to the reaction conditions.  $^{l"’b(0Ao)_}$4 .  o/  ,  R  (XI.)  a  (I). 