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Toluene → 2-Methyl-3b,4,6,7,7a,8-hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Toluene | HCID 1140 | — |
| 反応物 | 2-Bromo-3b,4,6,7,7a,8-hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester | HCID 59789467 | — |
| 反応物 | HCID 178477796 | HCID 178477796 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 2-Methyl-3b,4,6,7,7a,8-hexahydro-1-thia-5-aza-cyclopenta[alpha]indene-5-carboxylic acid ethyl ester | HCID 131727043 | 59% |
反応手順
A solution of the product from step b) (863 mg, 2.62 mmol) in dioxane (13.1 ml) was treated with Pd(dppf)2Cl2 (128 mg, 0.157 mmol) and a 2M solution of dimethylzinc in toluene (2.62 ml, 5.24 mmol) at 102° C. for 1 h. The reaction was cooled to 220C and carefully quenched with sat. NH4Cl (3 ml). After the effervescence subsided, the reaction was extracted with EtOAc (3×50 ml). The combined organic extracts were dried (MgSO4), concentrated and eluted through a plug of silica-gel using 50:50 hexanes:EtOAc to give 411 mg (59%) of the subtitle compound. MS calculated for C14H19NO2S+H 266, observed 266.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07423056B2 |
| 出典データセット | uspto-grants-2008_09 |
| ORD ID | ord-4a9651f0f37a433283832d5c0d96b434 |
| 出典メモ | uspto-grants-2008_09 |