HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → Compound 10
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Methyl morpholine oxide | HCID 82029 | — |
| Reactant | tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate | HCID 5148195 | — |
| Catalyst | Osmium Tetroxide | HCID 30318 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | Compound 10 | HCID 13329883 | — |
Reaction Steps
To a solution of N-t-butoxycarbonyl-3-pyrroline (69.3 g) and NMO (72.2 g) in tetrahydrofuran (340 mL), t-butanol (210 mL) and water (100 mL) was added OsO4 (2.5% solution in t-butanol, 4.8 mL), the mixture was heated under reflux for 2.5 hours, and then concentrated in vacuo. After dilution of the residue with brine, the mixture was extracted with ethyl acetate. The organic extracts were concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=1:1) of the residue gave
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07582659B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-fdc40ca763044be3acee1952944beda3 |
| Source note | uspto-grants-2009_09 |