1,10-Phenanthroline → (S)-3-(5,5-Dioxo-5H-5lambda6-dibenzothiophen-3-yloxy)-1-aza-bicyclo[2.2.2]octane

関与物質

役割	名称	HCID	仕込み量
反応物	1,10-Phenanthroline	HCID 1318	—
反応物	Cesium carbonate	HCID 10796	—
反応物	3-Quinuclidinol, (+)-	HCID 736411	—
反応物	3,7-Dibromo-dibenzothiophene 5,5-dioxide	HCID 4071898	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
溶媒	Toluene	HCID 1140	—
生成物	(S)-3-(5,5-Dioxo-5H-5lambda6-dibenzothiophen-3-yloxy)-1-aza-bicyclo[2.2.2]octane	HCID 57399776	63%

反応条件

温度	110 °C

反応手順

A mixture of 3,7-dibromodibenzothiophene-5,5-dioxide (0.60 g, 1.75 mmol; see J. Med. Chem. 1978, 21, 1084), (S)-(−)-quinuclidin-3-ol (280 mg, 2.2 mmol; Acros), copper (I) iodide (33 mg, 0.17 mmol; Aldrich), 1,10-phenanthroline (63 mg, 0.35 mol; Aldrich) and powdered cesium carbonate (0.86 g, 2.64 mmol; Aldrich) in toluene (2 mL) was heated to 110° C. with vigorous stirring for 30 h. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth, rinsing with ethyl acetate and dichloromethane, and the residue purified by flash chromatography (80 g silica gel, 1:10:89 NH4OH-MeOH—CH2Cl2) to afford the title compound (0.37 g, 1.08 mmol; 63% yield): MS (DCI/NH3): m/z 342 (M+1)+.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07951791B2
出典データセット	uspto-grants-2011_05
ORD ID	ord-d7b3f6a35ebe4305b45c46fa11f232cf
出典メモ	uspto-grants-2011_05