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

Participants

Reaction Steps

In a manner similar to the method described in example 1d, 4-(2-formyl-4-iodo-phenoxy)-piperidine -1-carboxylic acid tert-butyl ester (22 g, 51 mmol) prepared in Example 4a 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 (13.4 mL, 51 mmol), n-butyllithium (2.5 M, 25.7 mL, 51 mmol), trimethylsilyl chloride (8.09 mL, 51 mmol), triethylamine (11.7 mL, 66 mmol) and acetyl chloride (5.88 mL, 66 mmol) to give crude 1-[2-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-5-iodo-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Provenance & Evidence