D-Tartaric acid → (S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate)

Participants

Reaction Steps

(2S,3S)-2,3-Dihydroxysuccinic acid (0.23 g, 1.52 mmol) was added to a suspension of (R)-quinuclidin-3-yl 2-(4-fluorophenylamino)-2-phenylacetate (I8) (1.08 g, 3.05 mmol) in acetone (140 ml). The resulting mixture was heated at reflux and then allowed to cool at room temperature. The precipitate was collected by filtration to obtain (S)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) (689 mg, 45% yield, diastereomer 2 of 18). Evaporation of the mother solution gave (R)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) (535 mg, 41% yield, diastereomer 1 of I8).

Provenance & Evidence