HuagongsheHuagongshe Chemistry Print Report · For research reference only
(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine → (S)-6,8-Dibromochroman-4-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine | HCID 6612782 | — |
| Reactant | Triethylammonium formate | HCID 11084032 | — |
| Reactant | 6,8-Dibromochroman-4-one | HCID 53401189 | — |
| Catalyst | Dichloro(p-cymene)ruthenium(II) dimer | HCID 10908223 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-6,8-Dibromochroman-4-ol | HCID 67304261 | — |
Reaction Steps
To a mixture containing 6,8-dibromochroman-4-one in acetonitrile (0.3M) and 5/2 formic acid/triethylamine (30% by volume) was added (1S,2S)-(+)-N-p-tosyl-1,2-diphenylethylene diamine (1 mol %) and dichloro(p-cymene)-ruthenium (II) dimer (0.5 mol %). After stirring for 24 h, the reaction was diluted with ethylacetate and washed with brine/sodium bicarbonate (1:1). The organic phase was concentrated under reduced pressure to afford the title compound as a tan solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07973050B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-0ee4c634c6064be5b65f8e63bccbe2f0 |
| Source note | uspto-grants-2011_07 |