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

HRID 2207051Notes

Reaction equation

HRID 2207051 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 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.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture was stirred at 0° C. for 16 hrs
  3. washwashed with NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration and purification by flash column chromatography

Sources & evidence

ORD record
ord-cba5f6029ee04127bb6f85cfdf39d286
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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