Cesium carbonate → 1'-Butyl-3'-chloro-4-hydroxymethyl-4-phenyl-3,4,5,6-tetrahydro-2H,1'H-[1,4]bipyridinyl-2'-one

https://huagongshe.com/ko/reaction/516634

참여 물질

역할	이름	HCID	투입량
반응물	Cesium carbonate	HCID 10796	—
반응물	4-Phenylpiperidine-4-methanol	HCID 77896	—
반응물	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
반응물	Trifluoromethanesulfonic acid 1-butyl-3-chloro-2-oxo-1,2-dihydropyridin-4-yl ester	HCID 25221428	—
촉매	palladium(II) acetate	HCID 167845	—
용매	Water	HCID 962	—
용매	Dichloromethane	HCID 6344	—
용매	(Trifluoromethyl)benzene	HCID 7368	—
생성물	1'-Butyl-3'-chloro-4-hydroxymethyl-4-phenyl-3,4,5,6-tetrahydro-2H,1'H-[1,4]bipyridinyl-2'-one	HCID 59497081	—

반응 조건

온도	100 °C

반응 단계

4-Hydroxymethyl-4-phenylpiperidine (0.172 g, 0.9 mmol), palladium(II) acetate (0.007 g, 0.03 mmol), cesium carbonate (0.391 g, 1.2 mmol) and Xantphos (0.035 g, 0.06 mmol) were added to a solution of intermediate D9 (0.2 g, 0.6 mmol) in trifluoromethylbenzene (2 ml). The reaction mixture was heated at 100° C. for 24 hours in a sealed tube, after which it was cooled to room temperature. Subsequently, it was diluted with DCM, H2O (5 ml) and extracted with EtOAc (3×5 ml). The mixture was filtered through diatomaceous earth, and the filtrate was evaporated to dryness. The crude product was purified first by column chromatography (silica gel; eluent: DCM/EtOAc from 90/10 to 0/100) and then by reversed phase HPLC. The desired fractions were collected, evaporated in vacuo and finally freeze dried to yield compound E22 (0.041 g, 18%) as a white foam.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09114138B2
출처 데이터셋	uspto-grants-2015_08
ORD ID	ord-b68423f2e2fb4211b3f631f86f3b2c52
출처 메모	uspto-grants-2015_08