Diisopropylethylamine → HCID 67010368, compound

Participants

Reaction Steps

A mixture of (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-fluoro-2-methylbenzyl)pyrrolidine-2-carboxylic acid (540 mg, 1.54 mmol), prepared as in Reference 4, 4-(4-fluorophenoxy)aniline (313 mg, 1.54 mmol), DIEA (0.4 mL) and HATU (586 mg, 1.54 mmol) in DMF (3 mL) was stirred at ambient temperature for 1 hour. The mixture was diluted with ethyl acetate (100 mL), washed with saturated sodium bicarbonate (20 mL) and then brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. Product was purified from the residue by flash column (eluted with a 3:1 hexanes/ethyl acetate mixture) to give (2S,4R)-tert-butyl 4-(4-fluoro-2-methylbenzyl)-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidine-1-carboxylate (826 mg, 1.59 mmol, 103%) as a reddish oil.

Provenance & Evidence