HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → [2-(1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1H-indol-4-ol | HCID 75421 | — |
| Reactant | N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol | HCID 545700 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | [2-(1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl ester | HCID 10708626 | 70.7% |
Reaction Steps
To a cooled (0° C.) solution of 4-hydroxyindole (2.92 g) and (2-hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (3.50 g) in 100 mL of THF was added PPh3 (5.8 g) followed by the dropwise addition of diisopropylazodicarboxylate (4.44 g) over 10 minutes. After 16 h the reaction was worked up in the normal manner and the crude oil was purified by chromatography to afford 4.1 g of [2-(1H-indol-4-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester. MS: 313 (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07582760B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-654acd45167344d5af65693edff7b0a4 |
| Source note | uspto-grants-2009_09 |