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Triphenylphosphine → 4-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 3-[(Tert-butyldimethylsilyl)oxy]propan-1-ol | HCID 4077791 | — |
| 反応物 | 4-Chloro-5-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone | HCID 68488532 | — |
| 反応物 | ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene | HCID 87147022 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 4-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone | HCID 68490749 | 64% |
反応手順
In a similar manner to Step 1 of Example 149, 4-chloro-5-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (65.7 mg, 0.136 mmol) was dissolved in THF (3.5 mL), and the solution was treated with triphenylphosphine (178 mg, 0.680 mmol), 3-(tert-butyldimethylsiloxy)-1-propanol (0.145 mL, 0.680 mmol) and 40% DEAD-toluene solution (0.310 mL, 0.680 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=6/1) to obtain 4-chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (58.2 mg, yield 64%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745641B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-9af1a195deaf4ad9931e05ff98a8efdf |
| 出典メモ | uspto-grants-2010_06 |