HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triisopropyl borate → tert-butyl 4-(1H-indol-5-ylamino)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triisopropyl borate | HCID 21531 | — |
| Reactant | 1h-Indole-1-carboxylic acid,5-[[(1,1-dimethylethoxy)carbonyl][1-[(1,1-dimethylethoxy)carbonyl]-4-piperidinyl]amino]-,1,1-dimethylethyl ester | HCID 68493316 | — |
| Reactant | LDA THF ethylbenzene heptane | HCID 86590273 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-butyl 4-(1H-indol-5-ylamino)piperidine-1-carboxylate | HCID 66650318 | 62% |
Reaction Steps
In a similar manner to Step 2 of Reference Example 1, 5-[1-(tert-butoxycarbonyl)-4-piperidyl-N-(tert-butoxycarbonyl)amino]-1-(tert-butoxycarbonyl)indole (320 mg, 0.621 mmol) was dissolved in THF (5 mL), and the solution was treated with triisopropyl borate (0.215 mL, 0.932 mmol) and LDA-heptane/THF/ethylbenzene solution (2.0 mol/L, 0.776 mL, 1.55 mmol), followed by purification by slurry using hexane to obtain Compound BQ (177 mg, yield 62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07745641B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-7d2b35a6fcc24718a1fedb310af22cd2 |
| Source note | uspto-grants-2010_06 |