Abstract: A process of preparing lactam derivatives of pilocarpine is disclosed. The process involves condensation of a dihydroxybutene and alkyl orthoester to form a lactone intermediate which is oxidized to trans-pilopic acid. This lactone ring is reacted with a benzylamine and the benzyl group removed with a novel dissolving metal reduction mixture to yield the key intermediate IV ##STR1## which can be elaborated to pilolactam through a known sequence of steps.

Abstract: The invention is directed to a process for reducing or reductively cleaving an organic compound susceptible to dissolving metal reduction comprising exposing the organic compound to a solution of lithium in a polyamine including at least two amino groups, selected from the group consisting of primary and secondary amino groups and mixtures thereof, e.g. ethylenediamine and R--NH.sub.2, optionally containing a lower alkyl alcohol, wherein R is chosen from the group consisting of ethyl, propyl, and butyl, including all straight and branched chain isomers thereof, for a time sufficient to effect reduction.

Abstract: A process of preparing intermediates useful in making compounds with retinoic acid-like activity is disclosed. The intermediates are halogenated chromans and thiochromans of the formula shown below and are prepared by the alkylation of a phenol or thiophenol with an alkene compound (the starting materials shown in the formula below), cyclization and halogenation. ##STR1## In the formula the symbols have the following meanings: R.sub.1 and R.sub.2 are C.sub.1 to C.sub.4 alkyl, R.sub.3 is H or C.sub.1 to C.sub.4 alkyl, X is oxygen or sulfur, Y is a leaving group, and Z is chlorine, bromine or iodine.

Abstract: A process of preparing intermediates useful in making compounds with retinoic acid-like activity is disclosed. The intermediates are halogenated chromans and thiochromans of the formula shown below and are prepared by the alkylation of a phenol or thiophenol with an alkene compound (the starting materials shown in the formula below), cyclization and halogenation. ##STR1## In the formula the symbols have the following meanings: R.sub.1 and R.sub.2 are C.sub.1 to C.sub.4 alkyl, R.sub.3 is H or C.sub.1 to C.sub.4 alkyl, X is oxygen or sulfur, Y is a leaving group, and Z is chlorine, bromine or iodine.