HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (S)-1-(5-bromo-2,7-dimethylquinolin-6-yl)ethane-1,2-diol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | 1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine | HCID 51003674 | — |
| Reactant | 5-Bromo-2,7-dimethyl-6-vinylquinoline | HCID 66631391 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-1-(5-bromo-2,7-dimethylquinolin-6-yl)ethane-1,2-diol | HCID 66633145 | — |
Reaction Steps
AD-mix-α (8 g, excess) was added to a mixed solvent of t-butanol and water (35 mL/35 mL) and stirred at room temperature for 5 min, cooled to 0° C. 5-bromo-2,7-dimethyl-6-vinylquinoline (678 mg, 2.6 mmol) was added and the mixture was stirred at 0° C. for 16 hrs. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution, water and brine, and dried over Na2SO4. Concentration and purification by flash column chromatography yielded (S)-1-(5-bromo-2,7-dimethylquinolin-6-yl)ethane-1,2-diol. LCMS-ESI+ (m/z): [M+H]+ calc'd for C13H15BrNO2: 296.0; Found: 296.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376392B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-cba5f6029ee04127bb6f85cfdf39d286 |
| Source note | uspto-grants-2016_06 |