Acetyl chloride → 1-[5-Bromo-2-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Participants

Reaction Steps

In a manner similar to the method described in example 1d, 4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (5.5 g, 14.3 mmol) prepared in Example 15a was used as the starting material in place of 4-(2-formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester to react with 1,1,3,3,3-hexamethyldisilazane (3.97 mL, 14.3 mmol), n-butyllithium (2.5 M, 5.7 mL, 14.3 mmol), trimethylsilyl chloride (1.81 mL, 14.3 mmol), triethylamine (2.59 mL, 18.6 mmol) and acetyl chloride (1.31 mL, 18.6 mmol) to give crude 1-[5-bromo-2-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Provenance & Evidence