Water → (S)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol

HRID 2207019Notes

Reaction equation

HRID 2207019 reaction equation
CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.[C:59]([OH:63])(C)([CH3:61])[CH3:60].O.[Br:65][C:66]1C(C=C)=[C:74]([CH3:78])[CH:73]=[C:72]2[C:67]=1[CH:68]=[CH:69][CH:70]=[N:71]2>C(OCC)(=O)C>[Br:65][C:66]1[C:60]([C@H:59]([OH:63])[CH2:61][OH:22])=[C:74]([CH3:78])[CH:73]=[C:72]2[C:67]=1[CH:68]=[CH:69][CH:70]=[N:71]2

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 510036741-((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)phthalazineHCID 666306625-Bromo-7-methyl-6-vinylquinoline

Product 1

HCID 66631359(S)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

AD-mix-α (Aldrich, 0.7 g) was added to a mixed solvent of t-butanol and water (2.5 mL/2.5 mL) and stirred at 25° C. for 5 min, cooled to 0° C. The mixture was transferred to another flask containing 5-bromo-7-methyl-6-vinylquinoline (120 mg) and stirred at 0° C. for 48 hours. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc) to provide (S)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol. LCMS-ESI+ (m/z): 282.1, 284.1 (M+H)+.

Workup

  1. temperaturecooled to 0° C
  2. customThe mixture was transferred to another flask
  3. stirringstirred at 0° C. for 48 hours
  4. washwashed with NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (EtOAc)

Sources & evidence

ORD record
ord-0aa9a84531f4488a8c7fe0b8f9f78051
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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