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

HRID 2207031Notes

Reaction equation

HRID 2207031 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]1[C:75](C=C)=[C:74](C)[CH:73]=[C:72]2[C:67]=1[CH:68]=[CH:69][C:70]([CH3:79])=[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]([CH3:75])[CH:73]=[C:72]2[C:67]=1[CH:68]=[CH:69][C:70]([CH3:79])=[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 666313915-Bromo-2,7-dimethyl-6-vinylquinoline

Product 1

HCID 66633145(S)-1-(5-bromo-2,7-dimethylquinolin-6-yl)ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  1. temperaturecooled to 0° C
  2. stirringstirred at 0° C. for 16 hrs
  3. washwashed with NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4c2ce2b2b5fd42f780ef072fafb1efa0
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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