1,4-Bis(dihydroquinidine)phthalazine → (R)-1-(4-chloro-3-fluorophenyl)ethane-1,2-diol

HRID 1774144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774144
[Cl:1][C:2]1[CH:7]=[CH:6]C(C=C)=[CH:4][C:3]=1[F:10].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:32]C)C=C4)N(CC2)C1.[CH3:69][C:70]([OH:73])(C)[CH3:71].O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:69]([C@@H:70]([OH:73])[CH2:71][OH:32])=[CH:4][C:3]=1[F:10]

Komponenten

4

Edukt 3

HCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 199564661-Chloro-2-fluoro-4-vinylbenzeneHCID 714019492-Methylpropan-2-ol--water (1/1)

Produkt 1

HCID 86696646(R)-1-(4-chloro-3-fluorophenyl)ethane-1,2-diol

Versuchsvorschrift

1-Chloro-2-fluoro-4-vinylbenzene (12.1 g, 77.3 mmol) was added to a cold (0° C.) solution of AD-mix-β (108 g, 139 mmol) in t-BuOH/H2O (600 mL; 1:1), and the mixture was allowed to warm up to room temperature overnight. The next day, the reaction was placed in an ice bath and quenched with solid Na2SO3 (114 g). The mixture was stirred for 1 hour and then extracted with ethyl acetate (3×500 mL). The combined organics were dried, filtered and concentrated to give (R)-1-(4-chloro-3-fluorophenyl)ethane-1,2-diol as an oil. The crude product was used in Step C without purification.

Aufarbeitung

  1. customThe next day, the reaction was placed in an ice bath
  2. customquenched with solid Na2SO3 (114 g)
  3. extractionextracted with ethyl acetate (3×500 mL)
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5a5eee1250a247459ac6d24ce5fd2866
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09259470B2

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