Water → (S)-1-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethane-1,2-diol

HRID 931702Notes

Reaction equation

HRID 931702 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.[Cl:65][C:66]1[CH:75]=[C:74]2[C:69]([CH:70]=[CH:71][C:72]([CH3:76])=[N:73]2)=[C:68]([C:77]2[CH:82]=[CH:81][C:80]([Cl:83])=[CH:79][CH:78]=2)C=1C=C>C(OCC)(=O)C>[Cl:65][C:66]1[CH:75]=[C:74]2[C:69]([CH:70]=[CH:71][C:72]([CH3:76])=[N:73]2)=[C:68]([C:77]2[CH:82]=[CH:81][C:80]([Cl:83])=[CH:79][CH:78]=2)[C:60]=1[C@H:59]([OH:63])[CH2:61][OH:22]

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 666306227-Chloro-5-(4-chlorophenyl)-2-methyl-6-vinylquinoline

Product 1

HCID 66633446(S)-1-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)ethane-1,2-diolYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-5c815a5d76614fe789dcfaa6924e0a9a
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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