4-Amino-1-Boc-piperidine → 4-[3-(2H-tetrazol-5-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

In analogy to the procedure described in example 50k), N-piperidin-4-yl-3-(1H-tetrazol-5-yl)-benzamide [prepared from 3-(1H-tetrazol-5-yl)-benzoic acid by reaction with 4-amino-piperidine-carboxylic acid tert-butyl ester, N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride and N,N-dimethyl-4-aminopyridine in dichloromethane at rt in analogy to example 60d) to give 4-[3-(2H-tetrazol-5-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester followed by Boc cleavage in analogy to example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 469.4 (MH+).

Provenance & Evidence