Ammonia → HCID 54394851, compound

Participants

Reaction Steps

heating a mixture of an amine compound of the formula 4 ##STR4## and pure acid compound, formula 5 R1 ? ? ##STR5## at 200° C. for about 2 hours under argon or other inert gas to obtain amide compound 6 of the following formula ##STR6## (b) contacting compound 6 with phosphorous oxychloride to produce the 1,2-dehydro derivative of compound 7 shown below: ##STR7## which need not be isolated; (c) neutralizing the 1,2-dehydro derivative of compound 7 with aqueous ammonia and reducing with sodium cyanoborohydride or sodium borohydride to give racemic 7 which is then resolved by optically active acids to the compound tetrahydroisoquinoline (+)-7 to (-)-7 ##STR8## (d) treating of (-)-7 with lithium or sodium in liquid ammonia as a reducing agent to give hexahydroisoquinoline, compound (-)-8 ##STR9## and formylating compound (-)-8 to give 10 ##STR10## and introducing a protective group for the nitrogen in the subsequent steps of the reaction where the reagent for formylation of 8 to 10 is phenylformate chloral or ethyl formate

Provenance & Evidence