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

HRID 2365789노트

반응식

HRID 2365789 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b7bcbc4250604cb4954b64828f80ad76
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697715B2

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