HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (S)-1-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-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 | 7-Chloro-5-(4-chlorophenyl)-2-methyl-6-vinylquinoline | HCID 66630622 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-1-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethane-1,2-diol | HCID 66633446 | 84% |
Reaction Steps
AD-mix-α (1 g, excess) was added to a mixed solvent of t-butanol and water (4 mL/4 mL) and stirred at room temperature for 5 min and cooled to 0° C. The mixture was transferred to another flask containing 7-chloro-5-(4-chlorophenyl)-2-methyl-6-vinylquinoline (1G) (30 mg, 0.096 mmol) and stirred at 0° C. for 16 hours. 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 1H (28 mg, 84%). LCMS-ESI+ (m/z): 348.2, 350.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09296758B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-5c815a5d76614fe789dcfaa6924e0a9a |
| Source note | uspto-grants-2016_03 |