Potassium Phosphate, Tribasic → Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

참여 물질

역할	이름	HCID	투입량
반응물	Potassium Phosphate, Tribasic	HCID 62657	—
반응물	Lithium Chloride	HCID 433294	—
반응물	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine	HCID 2734648	—
반응물	8-Boc-3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-ene	HCID 22648094	—
촉매	[(1R,4S)-2-Bicyclo[2.2.1]heptanyl]-[(1S,4R)-2-bicyclo[2.2.1]heptanyl]phosphane;chloropalladium(1+);N,N-dimethyl-2-phenylaniline	HCID 11272965	—
용매	Water	HCID 962	—
용매	Ethyl Acetate	HCID 8857	—
용매	1,4-Dioxane	HCID 31275	—
생성물	Tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate	HCID 67268174	57.2%

반응 조건

온도	100 °C

반응 단계

1 g of tert-butyl 3-{[(trifluoromethyl)sulfonyl]oxy}-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate, 0.975 g of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 0.24 g of lithium chloride, 1.78 g of potassium phosphate, 0.157 g of 2′-(dimethylamino)-2-biphenylpalladium(II)chloride dinorbornylphosphine and 10 ml of dioxane are introduced into an 80 ml glass tube. The tube is sealed and then heated at 100° C. under microwave irradiation for 30 minutes. Water and ethyl acetate are added. The aqueous phase is extracted three times with ethyl acetate. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue is chromatographed on silica gel with a mixture of heptane/ethyl acetate. 0.458 g of tert-butyl 3-pyridin-4-yl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate is obtained.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07897773B2
출처 데이터셋	uspto-grants-2011_03
ORD ID	ord-d7bc2cbc67b743548d2b19506799ec94
출처 메모	uspto-grants-2011_03