HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethyl Ether → (2R)-2-t-Butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butanal
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Cornforth reagent | HCID 2724130 | — |
| Reactant | (2R)-2-t-Butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol | HCID 66672878 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2R)-2-t-Butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butanal | HCID 86596705 | 63% |
Reaction Steps
To a solution of (2R)-2-t-butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol (0.3520 g, 0.80 mmol) obtained in Example (43a) in dichloromethane (8 ml) were added successively molecular sieves 4A (0.2234 g) and pyridinium dichromate (0.4594 g, 1.22 mmol), and the resulting mixture was stirred at room temperature for 20 hours. After stirring, ether was added to the reaction mixture, and the resulting mixture was filtered. The filtrate was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (3:2) as the eluent to afford the title compound (0.2195 g, yield: 63%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101650B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-db7aba8fcfea4a45af3be3ec999bb203 |
| Source note | uspto-grants-2012_01 |