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

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

Reactant 3

HCID 11095166(3-Methyl-but-3-enyloxymethyl)-benzene

HCID 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)phthalazine

HCID 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.