Hydrochloric Acid → (1R)-2-[[3-(4-bromophenyl)propyl]-amino]-1-(3-pyridyl)ethanol

To a suspension of 3-(4-bromophenyl)-N-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]propanamide (3.42 g) in tetrahydrofuran (58 ml) was added 2.0M dimethyl sulfide—borane (1:1) in tetrahydrofuran (16.1 ml) dropwise at 0-5° C. over 45 minutes. After cooling to room temperature, to the reaction mixture were added methanol (2.99 ml) and 37% hydrochloric acid (4.8 ml) at 4° C. (ice bath). The mixture was stirred at 80° C. for 1 hour. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and to the residue was added water (100 ml). The pH was adjusted to 10 with 24% aqueous sodium hydroxide solution at 4° C. and the mixture was extracted with ethyl acetate (200 ml). The organic layer was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave (1R)-2-[[3-(4-bromophenyl)propyl]-amino]-1-(3-pyridyl)ethanol (3.22 g) as a yellow oil.

1. temperatureAfter cooling to room temperature
2. concentrationthe reaction mixture was concentrated under reduced pressure and to the residue
3. additionwas added water (100 ml)
4. customwas adjusted to 10 with 24% aqueous sodium hydroxide solution at 4° C.
5. extractionthe mixture was extracted with ethyl acetate (200 ml)
6. washThe organic layer was washed with water and brine
7. dry with materialdried over magnesium sulfate
8. filtrationFiltration
9. customfollowed by evaporation under reduced pressure

ORD record

ord-8e6fdd26b3f04fea8bbdaaa74828e0f5

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417060B2