Water → (S)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	tert-Butanol	HCID 6386	—
Reactant	1-((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 51003674	—
Reactant	5-Bromo-7-methyl-6-vinylquinoline	HCID 66630662	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(S)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol	HCID 66631359	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

AD-mix-α (0.7 g) was added to a mixed solvent of t-butanol and water (2.5 mL/2.5 mL) and stirred at 25° C. for 5 min, cooled to 0° C. The mixture was transferred to another flask containing 5-bromo-7-methyl-6-vinylquinoline (120 mg) and stirred at 0° C. for 48 hours. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc) to provide (S)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol (118 mg). LCMS-ESI+ (m/z): 282.1, 284.1 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09296758B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-81174d0c68534b65947981d1451a1edc
Source note	uspto-grants-2016_03