Hydrochloric Acid → Vilanterol

1N HCl (295 mL) was added to a solution of (R)-2-{6-[2-(2,6-dichlorobenzyloxy)-ethoxy]-hexylamino}-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-ethanol (52 g, 0.099 mol) in ethanol (312 mL), and the reaction stirred at ambient temperature for 1.5 h. Saturated sodium bicarbonate solution (500 mL) was added followed by dichloromethane (500 mL). The aqueous layer was separated and extracted with further dichloromethane (500 mL). The combined organic solutions were washed with water/brine mixture (500 mL/100 mL), then evaporated. The residue (50 g) was chromatographed on silica (800 g, Biotage) eluting with a dichloromethane/ethanol/ammonia mixture (50/8/1), to afford the title compound as an oil (35.2 g)—LC RT=4.1 min.

1. customThe aqueous layer was separated
2. extractionextracted with further dichloromethane (500 mL)
3. washThe combined organic solutions were washed with water/brine mixture (500 mL/100 mL)
4. customevaporated
5. customThe residue (50 g) was chromatographed on silica (800 g, Biotage)
6. washeluting with a dichloromethane/ethanol/ammonia mixture (50/8/1)

ORD record

ord-951c78745d2745d5ba4d48f651b279e0

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361787B2