Ethanolamine → (R)-1-(4-chloro-3-fluorophenyl)-2-(2-hydroxyethylamino)ethanol

(R)-2-(4-chloro-3-fluorophenyl)oxirane (1.66 g, 9.62 mmol) was added dropwise to ethanolamine (3.5 mL, 53.9 mmol). The (R)-2-(4-chloro-3-fluorophenyl)oxirane residue was rinsed with 4 mL of THF and this was added to the reaction mixture. The clear solution was stirred at room temperature for 48 h. TLC indicated complete consumption of the starting material. The mixture was treated with water (30 mL) under ice bath and then extracted with ethyl acetate (40 mL). The aqueous layer was extracted with ethyl acetate (30 mL). The combined organic phase was washed with water and brine, dried and concentrated in vacuo to afford (R)-1-(4-chloro-3-fluorophenyl)-2-(2-hydroxyethylamino)ethanol (2.06 g) as a colorless oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.54 (br. s., 3H) 2.64-2.77 (m, 1H) 2.84 (td, J=5.00, 3.59 Hz, 2H) 2.93 (dd, J=12.27, 3.59 Hz, 1H) 3.72 (t, J=5.10 Hz, 2H) 4.72 (dd, J=8.88, 3.59 Hz, 1H) 7.08 (dd, J=8.31, 1.89 Hz, 1H) 7.20 (dd, J=9.82, 1.89 Hz, 1H) 7.31-7.43 (m, 1H).

1. washThe (R)-2-(4-chloro-3-fluorophenyl)oxirane residue was rinsed with 4 mL of THF
2. additionthis was added to the reaction mixture
3. customconsumption of the starting material
4. additionThe mixture was treated with water (30 mL) under ice bath
5. extractionextracted with ethyl acetate (40 mL)
6. extractionThe aqueous layer was extracted with ethyl acetate (30 mL)
7. washThe combined organic phase was washed with water and brine
8. customdried
9. concentrationconcentrated in vacuo

ORD record

ord-44c3d3e764d0468a9121707760b01969

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353096B2