HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lawesson's reagent → 3-(R)-Tert-butyldimethylsilyloxy-4-(S)-(1-ethoxycarbonylcyclopropyl)-1-[1-(S)-phenylethyl]-2-pyrrolidinethione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | 3-(R)-Tert-butyldimethylsilyloxy-4-(S)-(1-ethoxycarbonylcyclopropyl)-1-[1-(S)-phenylethyl]-2-pyrrolidone | HCID 21971265 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | 3-(R)-Tert-butyldimethylsilyloxy-4-(S)-(1-ethoxycarbonylcyclopropyl)-1-[1-(S)-phenylethyl]-2-pyrrolidinethione | HCID 21971264 | 88% |
Reaction Steps
3-(R)-Tert-butyldimethylsilyloxy-4-(S)-(1-ethoxycarbonylcyclopropyl)-1-[1-(S)-phenylethyl]-2-pyrrolidone was dissolved in dry benzene (200 ml), and the solution was mixed with Lawesson's reagent (4.49 g, 11.1 mmol) and heated under reflux for 3 hours. After cooling, benzene was evaporated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=4:1, to thereby obtain 7.96 g (88%) of the title compound as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06121285 |
| Source dataset | uspto-grants-2000_09 |
| ORD ID | ord-2853368220f644a5a73847a8940ccabf |
| Source note | uspto-grants-2000_09 |