Ethylenediamine → (R)-3'-(4-Bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

참여 물질

역할	이름	HCID	투입량
반응물	Ethylenediamine	HCID 3301	—
반응물	Potassium Carbonate	HCID 11430	—
반응물	Thiophene, 2,4-dibromo-	HCID 2724560	—
반응물	AR-R-17779	HCID 5310971	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
용매	1,4-Dioxane	HCID 31275	—
생성물	(R)-3'-(4-Bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one	HCID 57634260	63.2%

반응 단계

(S)-Spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (471 mg, 2.58 mmol), 2,4-dibromothiophene (1.875 g, 7.75 mmole), copper (I) iodide (492 mg, 2.58 mmol), potassium carbonate (715 mg, 5.17 mmol) and ethylenediamine (170 μL, 2.58 mmol) in 1,4-dioxane (5 mL) were stirred at 110° C. overnight. The solution was allowed to cool, and then filtered, washed with aqueous ammonium hydroxide and evaporated. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound as a yellow solid (560 mg), m/z 343, 345 (MH+).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07514567B2
출처 데이터셋	uspto-grants-2009_04
ORD ID	ord-baaf5c4ddb024d939a8bda0714de2818
출처 메모	uspto-grants-2009_04