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

HRID 931702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931702
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]

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5c815a5d76614fe789dcfaa6924e0a9a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296758B2

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