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 stirred at 0° C. for 16 hrs. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product. LCMS-ESI+: calc'd for C13H14BrNO2: 296.0 (M+H+); Found: 296.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376392B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-4c2ce2b2b5fd42f780ef072fafb1efa0 |
| Source note | uspto-grants-2016_06 |