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Triacetoxyperiodinane → tert-Butyl 4-(4-phenyl-1,3-dioxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triacetoxyperiodinane | HCID 159087 | — |
| 反応物 | tert-Butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate | HCID 21983965 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | tert-Butyl 4-(4-phenyl-1,3-dioxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate | HCID 21983978 | 69.5% |
反応手順
To a solution of tert-butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (494 mg, 0.98 mmol) from Step F in methylene chloride (10 mL) at room temperature was added Dess-Martin reagent (621 mg, 1.5 mmol). After 3 h, the reaction was diluted with ether and quenched with 1N sodium hydroxide. After stirring for 30 min, the mixture was diluted with water and extracted twice with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate in hexanes) to afford the title product (343 mg).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07091211B2 |
| 出典データセット | uspto-grants-2006_08 |
| ORD ID | ord-0ad6df59fec94b07b829b6f097e8956d |
| 出典メモ | uspto-grants-2006_08 |