Ammonium Chloride → Tert-Butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-phenylpent-4-en-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottom flask containing tert-butyl (2S,3R)-3-hydroxy-1-phenylpent-4-en-2-ylcarbamate (3.080 g, 11 mmol) was added DCM (50 mL) and the mixture was allowed to stir at 23° C. for 2 min. At this time, TEA (4.7 ml, 33 mmol) was added via syringe before dropwise addition of tert-butyldimethylsilyl triflate (2.8 ml, 12 mmol). The reaction was allowed to stir for 4 h and then poured into saturated ammonium chloride. The aqueous layer was extracted with DCM (3×75 mL) and the combined organics were washed with brine and dried with sodium sulfate. The solution was filtered and concentrated to provide 4.47 g of a yellow solid. The material was taken on to the next step without any further purification.

Provenance & Evidence