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1-Hydroxybenzotriazole → [4-(Pyrrolidin-1-yl)piperidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | 4-(1-Pyrrolidinyl)piperidine | HCID 78703 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 反応物 | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid | HCID 2734621 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | [4-(Pyrrolidin-1-yl)piperidin-1-yl][4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone | HCID 57886103 | 42% |
反応手順
A solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid (9.80 mmol, 2.43 g), 4-(1-pyrrolidinyl)piperidine (10.77 mol, 1.66 g), 1-hydroxybenzotriazole (16.67 mmol, 2.25 g), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (19.57 mmol, 3.75 g) in DMF (30 mL) was stirred overnight at 60° C. Upon removal of DMF on rotavap, the residue was taken into mixture of EtOAc and H2O. The combined organic layers from extraction were stirred with aq. 2N HCl for 20 min and the aqueous layer was purified by reverse phase prep-HPLC to furnish the desired boronic acid (1.24 g. 42%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08846664B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-2b9a53560a5e4de0a9233069280129c6 |
| 出典メモ | uspto-grants-2014_09 |