Hydrochloric Acid → HCID 67170876, compound

Participants

Reaction Conditions

Reaction Steps

To (±)-2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetonitrile (Preparation 131A, 1.1 g, 2.5 mmol) in dioxane (18.0 mL) was added water (12.0 mL) and hydrochloric acid, 37% (12 mL). The reaction mixture was heated at 100° C. for 3 h. After cooling, it was concentrated to provide the product as a racemic mixture. LC/MS M+1=458.0. The individual enantiomers were separated using a chiral preparative column under SFC conditions (Chiralcel OJ-H 5×25 cm, column temperature 20° C., isocratic elution with mobile phase 35% acetonitrile+0.1 TFA in CO2, 280 mL/min, 250 nM). Isomer 1 (500 mgs), retention time on chiral HPLC, 7.26 min; Isomer 2 (600 mgs), retention time on chiral HPLC, 9.88 min. The absolute stereochemistry at the carbon anchoring the secondary alcohol, of Isomer 1 and Isomer 2 was not determined.

Provenance & Evidence