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

HRID 1896968Notes

Reaction equation

HRID 1896968 reaction equation
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

Participants

4

Reactant 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)

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a25a6efb0e534090a3c8546e3bc86582
Source dataset
uspto-grants-2013_08
Patent number
US08518984B2

Reaction notes

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