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Triphenylphosphine → ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 2,6-Dimethyl-3-pyridinol | HCID 70732 | — |
| 反応物 | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| 反応物 | ethyl [(1S)-5-(2-hydroxyethoxy)-2,3-dihydro-1H-inden-1-yl]acetate | HCID 59300449 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate | HCID 59300516 | 84% |
反応手順
To a solution of ethyl [(1S)-5-(2-hydroxyethoxy)2,3-dihydro-1H-inden-1-yl]acetate (Example 249, 50.0 mg, 0.19 mmol) and 2,6-dimethylpyridin-3-ol (46.6 mg, 0.38 mmol) in THF (1.5 mL) were added PPh3 (99.2 mg, 0.38 mmol) and ADDP (95.5 mg, 0.38 mmol). The reaction mixture was vigorously stirred at rt for 24 h, and then directly applied to a silica gel column for purification (1:1 hexanes/EtOAc) to give the product (58.9 mg, 84%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.29 (t, 3H) 1.72-1.81 (m, 1H), 2.36-2.2.44 (m, 2H), 2.45 (s, 3H), 2.47 (s, 3H), 2.73 (dd, 1H) 2.82-2.92 (m, 2H), 3.52-3.56 (m, 1H) 4.19 (q, 2H), 4.26-4.33 (m, 4H), 6.75 (d, 1H), 6.82 (s, 1H) 6.92 (d, 1H), 7.05 (d, 1H), 7.08 (d, 1H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07714004B2 |
| 出典データセット | uspto-grants-2010_05 |
| ORD ID | ord-99ced311783e4077b126db39288c8e33 |
| 出典メモ | uspto-grants-2010_05 |