Methanol → HCID 86630358, compound

Temperature

90 °C

To a solution of the compound (2.00 g) obtained in step 5 in THF (30 mL) was added 1M BH3.THF complex/THF solution (32.0 mL) at 0° C., and the mixture was stirred at 90° C. for 1 hr. After the reaction mixture was cooled to 10° C., MeOH (10 mL) was added, and the mixture was concentrated under reduced pressure. The residue was suspended in 6N hydrochloric acid (32 mL), and the mixture was stirred at 100° C. for 2 hr. The reaction mixture was cooled to 10° C., and made basic with aqueous sodium hydroxide solution, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 33→50% ethyl acetate/hexane) to give 2-(benzyl(2-(2-chloropyridin-3-yl)ethyl)amino)ethanol (0.88 g, 46%) as a colorless oil.

1. temperatureAfter the reaction mixture was cooled to 10° C.
2. concentrationthe mixture was concentrated under reduced pressure
3. stirringthe mixture was stirred at 100° C. for 2 hr
4. temperatureThe reaction mixture was cooled to 10° C.
5. extractionthe resultant product was extracted with ethyl acetate
6. washThe organic layer was washed with brine
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography (solvent gradient; 33→50% ethyl acetate/hexane)

ORD record

ord-12638db417e443fca1e0f1e54df1c604

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079907B2