2-[2-(Tert-butyldimethylsilanyloxy)ethyl]-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazine-1-carboxylic acid tert-butyl ester → 2-(2-Hydroxyethyl)-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)piperazine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A solution of 2-[2-(tert-butyldimethylsilanyloxy)ethyl]-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazine-1-carboxylic acid tert-butyl ester, 59, (15.9 g, 23.5 mmol) and 1 M tetrabutylammonium fluoride (40 mL) is stirred for 24 hours. The reaction solution is filtered through a pad of silica gel, the filtrate is concentrated in vacuo, and the resulting crude product purified over silica gel (EtOAc/hexane 1:2, 1:1, then 5% methanol in EtOAc) to afford the desired product.

Provenance & Evidence