(R)-1-N-Boc-2-(hydroxymethyl)piperazine

(R)-tert-Butyl 2-(hydroxymethyl)piperazine-1-carboxylate is used in preparation of novel substituted quinoline-8-carbonitrile derivatives with androgen receptor degradation activity and uses thereof.

Lithium aluminum hydride (1M in THF, 26 ml) was added to a solution of L-TERT- butyl 2-methyl (2R)-piperazine-1, 2-dicarboxylate (2. 55 g) in THF (70 ml) at-40°C, and then the reaction was warmed to room temperature. After stirring for 1 h, this reaction system was cooled to 0°C and quenched by sequential addition of water (1 ml), sodium hydroxide (2N, 1 ml), and then water (2 ml). The resulting slurry was filtered and concentrated in vacuo to give (R)-1-N-Boc-2-(hydroxymethyl)piperazine.