化工社化工社 化学情報印刷レポート · 研究参考用
HRID 79174作成日：2026年10月24日
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 5-(4-((t-Butyldimethylsilyloxy)methyl)piperidin-1-yl)-2-chloropyridine
https://huagongshe.com/ja/reaction/79174
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | 5-Bromo-2-chloropyridine | HCID 2734414 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 反応物 | 4-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidine | HCID 67021994 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 5-(4-((t-Butyldimethylsilyloxy)methyl)piperidin-1-yl)-2-chloropyridine | HCID 58299561 | 9% |
反応手順
5-Bromo-2-chloropyridine (1.00 g, 5.20 mmol), 4-((t-butyldimethylsilyloxy)-methyl)piperidine (284), (1.19 g, 5.20 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0952 g, 0.104 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.180 g, 0.312 mmol), and sodium t-butoxide (0.749 g, 7.79 mmol) were dissolved in 40 mL dioxane under argon. The reaction was heated at 80° C. for 17 hours. The resulting solution was cooled an taken up in ethyl acetate (125 mL) and washed with aqueous K2CO3, (10%, 100 mL) water (100 mLl), and brine (100 mL). The organic phase was dried (MgSO4) and evaporated to give an orange oil. Silica gel chromatography (gradient elution hexanes/0-10% ethyl acetate) afforded compound 281 as a white solid (158 mg, 9%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08841312B2 |
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| 出典データセット | uspto-grants-2014_09 |
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| ORD ID | ord-3e70ebf4908c4062bfabef48501f60d9 |
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| 出典メモ | uspto-grants-2014_09 |
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