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

HRID 2365789Notes

Reaction equation

HRID 2365789 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b7bcbc4250604cb4954b64828f80ad76
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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