Lithium Chloride → HCID 57659753, compound

Participants

Reaction Steps

Lithium chloride (1.21 g, 28.49 mmol) and sodium borohydride (1.08 g, 28.49 mmol) were added to a solution of (4) in (4.44 g, 9.49 mmol) in methanol (50 ml) at RT. The reaction was stirred overnight 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. The resulting crude product was purified via column chromatography using ethyl acetate/hexane gradients to yield ((2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidin-2-yl)methanol (5) (2.23 g, 53%) as a white solid. MS m/z 440.2 (M+H)+; retention time=3.006 min, method [1].

Provenance & Evidence