Water → HCID 59432155, compound

Participants

Reaction Steps

460 mg (1.5 mmol) of methyl 2-(4-fluoro-2-trifluoromethylbenzoylamino)but-3-enoate were dissolved in tert-butanol/water, and 360 mg (3 mmol) of N-methylmorpholine N-oxide and 1.5 g (0.15 mmol) of a 2.5% strength solution of OsO4 in tert-butanol were added. The mixture was stirred at RT for 60 hours. 3.2 g of sodium sulfite, water and ethyl acetate were then added, and the phases were separated. The aqueous phase was reextracted with ethyl acetate. The combined organic phases were washed and dried, and the solvent was removed. This gave 440 mg (86% of theory) of crude product (diastereomer ratio about 2:1) which was used for the next step without further purification.

Provenance & Evidence