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Binap, (A+-)- → (3R)-3-methyl-1-(1H,3H-naphtho[1,8-cd]pyran-6-yl)piperazine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Binap, (A+-)- | HCID 634876 | — |
| 反応物 | 2-Methylpiperazine, (R)- | HCID 7330434 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 反応物 | 6-bromo-1H,3H-naphtho[1,8-cd]pyran | HCID 69307283 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | (3R)-3-methyl-1-(1H,3H-naphtho[1,8-cd]pyran-6-yl)piperazine | HCID 69306502 | — |
反応手順
A mixture of 6-bromo-1H,3H-naphtho[1,8-cd]pyran (0.30 g, 1.2 mmol), 2-(R)-methylpiperazine (0.145 g, 1.44 mmol), tris(dibenzylideneacetone)dipalladium(0) (55 mg, 0.06 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (56 mg, 0.09 mmol) and sodium tert-butoxide (0.162 g, 1.68 mmol) in toluene (5 mL) was heated under reflux for 2 h. The solvent was evaporated in vacuo and the crude mixture purified by column chromatography on silica gel, eluting with dichloromethane/methanol (9:1), to yield (3R)-3-methyl-1-(1H,3H-naphtho[1,8-cd]pyran-6-yl)piperazine as an orange solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07335660B2 |
| 出典データセット | uspto-grants-2008_02 |
| ORD ID | ord-3246601d97494adcb52ff263b8e80177 |
| 出典メモ | uspto-grants-2008_02 |