Imidazole → HCID 57659768, compound

Participants

Reaction Steps

t-Butyldimethylsilyl chloride (TBSCl) (4.07 g, 27.03 mmol) and imidazole (2.58 g, 37.8 mmol) were added to a solution of (3) (9.55 g, 27.03 mmol) in DMF (60 ml) at RT. The reaction was stirred for 4 hours and concentrated in vacuo. The residue was dissolved in EtOAc and washed with 0.1M aqueous HCl, sat. sodium bicarbonate solution and brine. The organic layers were dried with sodium sulfate and concentrated in vacuo to yield (2S,4R)-methyl 4-(tert-butyldimethylsilyloxy)-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxylate (4) (11.83 g, 94%) as a yellow oil. It was used without further purification in the next step. MS m/z 490.2. (M+Na)+; retention time=3.159 min, method [1].

Provenance & Evidence