Hydrochloric Acid → HCID 66882355, compound

Participants

Reaction Steps

A solution of 600 mg (2.9 mmol) of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (prepared according to C. F. Bigge et al., patent application WO 2003045912) in 10 ml of THF was cooled to −78° C. and treated dropwise with 3.2 ml of a 1M lithium bis(trimethylsilyl)amide-solution in THF and stirred for 30 min. To this solution 500 mg (3.2 mmol) of (1SR,5SR,6SR) 2-oxo-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester dissolved in 5m of THF were added portionwise. The mixture was allowed to reach RT and stirred for 10 hrs. The mixture was then poured into a diluted aqueous HCl-solution (ca. 0.2 M) and extracted with AcOEt. The combined organic phases were dried with Na2SO4. Filtration, evaporation of the solvent gave 630 mg (57%) of (1SR,2SR,3RS) 2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-3-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester. Orange foam. MS: 373 (M−H)−.

Provenance & Evidence