Acetyl chloride → (R/S)-1-[5-bromo-2-(1-tert-butoxycarbonyl-3-pyrrolidinyloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Participants

Reaction Steps

In a manner similar to the method described in example 1d, (R/S)-3-(4-bromo-2-formyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (2.7 g, 7.4 mmol) 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 (1.2 g, 7.4 mmol), n-butyllithium (2.5 M, 3 mL, 7.5 mmol), trimethylsilyl chloride (0.8 g, 7.4 mmol), triethylamine (1 g, 10 mmol) and acetyl chloride (0.79 g, 10 mmol) to give crude (R/S)-1-[5-bromo-2-(1-tert-butoxycarbonyl-3-pyrrolidinyloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Provenance & Evidence