HuagongsheHuagongshe Chemistry Print Report · For research reference only
Imidazole → 5-{[2-(Tert-butyldimethylsilyloxy)ethyl]aminomethyl}-1-(tert-butoxycarbonyl)indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | HCID 68492342 | HCID 68492342 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-{[2-(Tert-butyldimethylsilyloxy)ethyl]aminomethyl}-1-(tert-butoxycarbonyl)indole | HCID 68493476 | 86% |
Reaction Steps
In a similar manner to Step 1 of Reference Example 18, 5-[(2-hydroxyethyl)aminomethyl]-1-(tert-butoxycarbonyl)indole (5.40 g) was dissolved in DMF (50 mL) and the solution was treated with imidazole (940 mg, 13.8 mmol) and tert-butyl dimethylsilylchloride (2.08 g, 13.8 mmol), followed by purification by slurry using diisopropyl ether and hexane to obtain 5-{[2-(tert-butyldimethylsilyloxy)ethyl]aminomethyl}-1-(tert-butoxycarbonyl)indole (4.80 g, yield 86%, 2 steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07745641B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-828e6addb0fe41f8b64fb2929a0e6766 |
| Source note | uspto-grants-2010_06 |