Diisopropylethylamine → HCID 89690304, compound

Participants

Reaction Conditions

Reaction Steps

Add diisopropylethylamine (57 mL, 327 mmol) to a suspension of 3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-aniline hydrochloride (90 g, 175 mmol) in THF (450 mL). To this mixture, add dihydro-3,3-dimethyl-2,5-furandione (32.1 g, 251 mmol) and stir at 35° C. until LCMS indicates 5% starting material remaining. Concentrate the mixture in vacuo and add methyl tert-butyl ether (100 mL) and water (75 mL). Adjust to pH=2-3 with phosphoric acid and separate the layers. Wash the aqueous layer with additional methyl tert-butyl ether (2×50 mL). Wash the combined organic extracts with brine and concentrate in vacuo. Dissolve the crude residue in methyl tert-butyl ether (180 mL) and add hexane (450 mL) to obtain a suspension and stir for 30 min. Collect the suspension by filtration and dry to yield the title compound (92.5 g, 88%) as a white solid. ES/MS m/z 642 (M+1).

Provenance & Evidence