Trimethylamine oxide → HCID 118161664, compound

Participants

Reaction Steps

To an ice-cooled solution of trimethylamine oxide (717 mg, 9.55 mmol) and 5-((1S,5R,6S)-bicyclo[3.1.0]hex-2-en-6-yl)-3-iodo-1-isopropyl-1H-pyrazole (2.0 g, 6.4 mmol) in tetrahydrofuran (10 mL) under nitrogen was added lithium diisopropylamide (28 mmol). After 1 h at 0° C., the reaction mixture was diluted with water (50 mL), and the resulting solution was extracted with ethyl acetate (2×20 mL). The collected organic was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (17% ethyl acetate in petroleum ether) afforded a brown oil (110 mg, 4.7%). LCMS (ESI): [MH]+=372.2.

Provenance & Evidence