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Diethylene glycol vinyl ether → tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diethylene glycol vinyl ether | HCID 13581 | — |
| 反応物 | Tert-butyl but-3-en-1-yl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)carbamate | HCID 131735521 | — |
| 触媒 | (1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichloride | HCID 11147261 | — |
| 溶媒 | Methylcyclohexane | HCID 7962 | — |
| 生成物 | tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate | HCID 68054971 | — |
反応手順
A solution of Example 87B (7.28 g, 20.72 mmol) in methyl cyclohexane (1.5 L) was degassed with nitrogen and (1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium (250 mg, 0.294 mmol) was added. The mixture was stirred at room temperature overnight and diethyleneglycol vinyl ether (0.16 mL) was added to inactivate any remaining active catalyst. The mixture was stirred for 30 minutes, concentrated and purified by flash chromatography on silica using an Analogix system (0-10% ethyl acetate/heptane) to provide the title compound. MS (ESI+) m/z 346 (M+Na)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09328112B2 |
| 出典データセット | uspto-grants-2016_05 |
| ORD ID | ord-4eb3b16da39049bb9d025d1ac48bcd79 |
| 出典メモ | uspto-grants-2016_05 |