Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → Piperidine-1-carboxamidine

Participants

Reaction Steps

Scheme XIXb outlines the synthesis of the analogous compounds where R1 is 4-(1-amidinopiperidinyl) instead of 4-amidinophenyl. After initial condensation of N-BOC-4-piperidinylcarbinol with methyl 3-hydroxyisoxazole-5-carboxylate under Mitsunobu conditions, the intermediate ester is saponified and condensed with a 1,3-diaminpropionate using conditions described above. The piperidine nitrogen is deprotected and treated with N,N'-diCBz-S-methylisothiourea to give a protected amidinopiperdine. Hydrogenation gives the amidinopiperidine compounds as the methyl esters. ##STR76##

Provenance & Evidence