HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 4-(2-Pyridinesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 86628320 | HCID 86628320 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4-(2-Pyridinesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone | HCID 86628321 | 32% |
Reaction Steps
In a similar manner to Step 2 of Example 6, 4-(2-pyridinesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.332 g, 0.589 mmol) was dissolved in acetonitrile (10.0 mL), and the solution was treated with pyrrolidine (0.983 mL, 11.8 mmol), acetic acid (0.674 mL, 11.8 mmol) and sodium triacetoxyborohydride (0.375 g, 1.77 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=85/15) to obtain 4-(2-pyridinesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone (0.116 g, 32%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07745641B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-ca5cd20c1eca451aaef482280573bc8d |
| Source note | uspto-grants-2010_06 |