Triphosgene → HCID 67295246, compound

Temperature

0 °C

To a suspension of (R)-2-amino-2-(5-bromopyridin-2-yl)ethanol hydrogen chloride (4.97 g, 19.6 mmol) and TEA (9.02 mL, 64.7 mmol) in DCM (60 mL) at 0° C. was added a solution of triphosgene (2.91 g, 9.80 mmol) in DCM (20 mL) during 45 min. The resulting mixture was stirred at 0° C. for 15 min, then warmed to it and stirred for 1 h. The reaction was quenched with NH4Cl (15 mL) and stirred for 15 min. The aqueous layer was separated, basicified with Na2CO3, and extracted with DCM (×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by a SiO2 column (0-80% EtOAc/Hexanes, Rf=0.15 in 50% EtOAc) to afford the titled compound as an off-white solid (3.60 g).

1. temperaturewarmed to it
2. stirringstirred for 1 h
3. customThe reaction was quenched with NH4Cl (15 mL)
4. stirringstirred for 15 min
5. customThe aqueous layer was separated
6. extractionextracted with DCM (×3)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. customThe crude product was purified by a SiO2 column (0-80% EtOAc/Hexanes, Rf=0.15 in 50% EtOAc)

ORD record

ord-e8c3eba1be4544a988ec43559982261e

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227971B2