Triethylamine → (S)-1-(2-(5-((3,4-Dimethoxyphenoxy)methyl)oxazol-2-yl)pyrrolidin-1-yl)-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone

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Reaction Steps

To a solution of 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetic acid (0.075 g) and Et3N (0.038 ml) in THF (1 ml), ethyl chloroformate (0.028 g) was added over an ice bath, followed by stirring at the same temperature for an hour. To the reaction mixture, a solution of (S)-5-((3,4-dimethoxyphenoxy)methyl)-2-(pyrrolidin-2-yl)oxazole (0.075 g) in THF (1 ml) was added over an ice bath, followed by stirring at room temperature for 15 hours. After adding water and performing extraction with AcOEt, the organic layer was washed with saturated aqueous sodium chloride, dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (0.104 g, colorless amorphous.)

Provenance & Evidence