HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Dioxaspiro[4.5]decan-8-one → 8-Methylidene-1,4-dioxaspiro[4.5]decane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,4-Dioxaspiro[4.5]decan-8-one | HCID 567415 | — |
| Reactant | Lithium | HCID 3028194 | — |
| Reactant | 1-(3-Nitropyridin-2-yl)piperidin-4-one | HCID 3510540 | — |
| Reactant | 2-(4-Methylene-1-piperidyl)-3-nitropyridine | HCID 57493809 | — |
| Reactant | Lithium bistrimethylsilylamide | HCID 86605622 | — |
| Product | 8-Methylidene-1,4-dioxaspiro[4.5]decane | HCID 10953743 | — |
Reaction Steps
The title compound was prepared following the method reported here for Compound 2a, but using lithium-bis-trimethylsilylamide instead of buthyl lithium and carrying out the reaction at −20° C. As starting material 1,4-dioxaspiro[4.5]decan-8-one replaced 1-(3-nitro-2-pyridyl)-4-oxopiperidine. After the usual work-up procedure the residue was purified by means of automated flash chromatography (Horizon®TM-Biotage; Petroleum Ether EtOAc 95:5) to give the title compound as fluid colourless oil. Yield: 99.3%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08580962B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-f3699746ad754c4499ad5b4d69347e4b |
| Source note | uspto-grants-2013_11 |