Ethyl Acetate → (S)-2-(5-Bromo-2-fluoro-phenyl)-propane-1,2-diol

HRID 39229

Reaktionsgleichung

Reaktionsgleichung von HRID 39229
[C:1]([O-:4])([O-])=O.[K+].[K+].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(OC)C=C4)N(CC2)C1.[Br:65][C:66]1[CH:71]=[CH:70][C:69]([F:72])=[C:68](C(C)=C)[CH:67]=1.CCO[C:79]([CH3:81])=[O:80]>C(O)(C)(C)C.O>[Br:65][C:66]1[CH:67]=[CH:68][C:69]([F:72])=[C:70]([C@@:79]([OH:80])([CH3:81])[CH2:1][OH:4])[CH:71]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 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 585629224-Bromo-1-fluoro-2-isopropenyl-benzene

Produkt 1

HCID 66665442(S)-2-(5-Bromo-2-fluoro-phenyl)-propane-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of K3Fe(CN)6 (186 g, 561 mmol), K2CO3 (78 g, 561 mmol), (DHQ)2-PHAL (1.311 g, 1.674 mmol) and K2OsO2(OH)4 (0.378 g, 1 mmol) in t-BuOH—H2O 1:1 (1600 ml) was added 4-bromo-1-fluoro-2-isopropenyl-benzene (36 g, 167 mmol) at 0° C. and the reaction mixture was stirred for 14 h at 0° C. After careful addition of Na2S2O5 (100 g) at 0-5° C. the reaction mixture was stirred for 1 h before extraction with EtOAc. Combined extracts were washed with 5% NaS3O3 solution and brine, dried over MgSO4, filtered and concentrated to give the title compound as a white solid: TLC (hexane-EtOAc 1:1): Rf=0.46; UPLC RtH5=0.767 min; ESIMS: 266, 268 [(M+NH4)+]; 1H NMR (360 MHz, CDCl3): δ 7.71 (dd, 1H), 7.27 (m, 1H), 6.83 (dd, 1H), 3.85 (d, 1H), 3.62 (d, 1H), 2.94 (s, 3H), 2.01 (s, 1H), 1.43 (s, 3H).

Aufarbeitung

  1. washCombined extracts were washed with 5% NaS3O3 solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f6f56923d2774a2ea89a8c7acb657ab6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524897B2

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