Lithium Hexamethyldisilazide → HCID 71117334, compound

Participants

Reaction Steps

A 500-mL, three-necked, round-bottomed flask was charged with cis-methyl 2-((4-fluorophenyl)amino)cyclopentanecarboxylate (racemic cis-17A′) (15.77 g, 66.5 mmol) and 75 mL of THF. The reaction mixture was cooled at 5° C. while a 1M solution of LiHMDS (73.1 mL, 73.1 mmol) was added dropwise via syringe over 10 min. The resulting reaction mixture was stirred at 5° C. to 15° C. for 1.5 h. The reaction mixture was then quenched into 200 mL of aqueous ammonium chloride and 250 mL of ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give 14 g of cis-6-(4-fluorophenyl)-6-azabicyclo[3.2.0]heptan-7-one (racemic 17DP) as an orange oil.

Provenance & Evidence