(3-Methyl-but-3-enyloxymethyl)-benzene → (S)-4-(benzyloxy)-2-methylbutane-1,2-diol

HRID 332072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332072
CC(=C)C[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.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:35]C)C=C4)N(CC2)C1.[CH3:72][C:73]([OH:76])([CH3:75])[CH3:74].O>>[CH2:6]([O:5][CH2:4][CH2:72][C@:73]([CH3:75])([OH:76])[CH2:74][OH:35])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 3

HCID 11095166(3-Methyl-but-3-enyloxymethyl)-benzeneHCID 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 714019492-Methylpropan-2-ol--water (1/1)

Produkt 1

HCID 67205693(S)-4-(benzyloxy)-2-methylbutane-1,2-diol

Versuchsvorschrift

Compound 1 was added to a solution of AD-mix-α in tBuOH/H2O (1:1) cooled in an ice bath. After TCL monitoring showed the disappearance of the starting material, the reaction was quenched by adding Na2SO3. The aqueous phase was extracted with ethyl acetate three times and the combined organic phase was washed with brine and dried (Na2SO4). The solid was filtered and the solvent was removed. The residue was purified by column chromatography to give compound 2.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customthe reaction was quenched
  3. additionby adding Na2SO3
  4. extractionThe aqueous phase was extracted with ethyl acetate three times
  5. washthe combined organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationThe solid was filtered
  8. customthe solvent was removed
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-401cd47f701847db96bc095f71c65c2d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877796B2

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