HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropylethanediol → 4-(2-Isopropoxyethoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropylethanediol | HCID 7996 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone | HCID 68493222 | — |
| Reactant | ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene | HCID 87147022 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(2-Isopropoxyethoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone | HCID 68489219 | 59% |
Reaction Steps
In a similar manner to Step 1 of Example 149, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.102 g, 0.221 mmol) was dissolved in THF (5.1 mL), and the solution was treated with triphenylphosphine (0.116 g, 0.442 mmol), 40% DEAD-toluene solution (0.201 mL, 0.442 mmol) and 2-isopropoxyethanol (0.126 mL, 1.10 mmol), followed by purification by flash column chromatography (chloroform/methanol=4/1) to obtain 4-(2-isopropoxyethoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0677 g, yield 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07745641B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-6e225a67e24449ef8230cc4ada17c364 |
| Source note | uspto-grants-2010_06 |