関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | (1R,2R)-2-Aminocyclohexanol | HCID 735777 | — |
| 反応物 | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| 反応物 | (3,5-Difluorophenyl)boronic acid | HCID 2734338 | — |
| 反応物 | 3-Iodooxetane | HCID 13356686 | — |
| 触媒 | Nickel(II) iodide | HCID 26038 | — |
| 溶媒 | Isopropanol | HCID 3776 | — |
| 生成物 | 3-(3,5-Difluorophenyl)oxetane | HCID 70655340 | 63% |
反応手順
3,5-difluorophenylboronic acid (2.0 equiv.), (1R,2R)-2-aminocyclohexanol (0.06 equiv.), NaHMDS (2.0 equiv.), and nickel(II) iodide (0.06 equiv.) were dissolved in 2-propanol (0.35 M). The mixture was degassed with N2, stirred at rt for 10 min and then a solution of 3-iodooxetane (1.0 equiv.) in 2-Propanol (0.70 M) was added. The mixture was sealed and heated at 80° C. in the microwave for 20 min. The mixture was filtered through celite, eluting with EtOH and concentrated. The crude residue was purified by ISCO SiO2 chromatography eluting with 0-100% EtOAc in Heptanes to afford 3-(3,5-difluorophenyl)oxetane in 63% yield. 1H NMR (400 MHz, <cdcl3>) δ 6.88-6.96 (m, 2H), 6.72 (tt, J=2.20, 8.95 Hz, 1H), 5.08 (dd, J=6.26, 8.22 Hz, 2H), 4.71 (t, J=6.26 Hz, 2H), 4.14-4.24 (m, 1H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09173883B2 |
|---|
| 出典データセット | uspto-grants-2015_11 |
|---|
| ORD ID | ord-43df638c606d45588962237d0b98474b |
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| 出典メモ | uspto-grants-2015_11 |
|---|
