tert-Butanol → (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane

Participants

Role	Name	HCID	Charge
Reactant	tert-Butanol	HCID 6386	—
Reactant	Sodium Sulfite	HCID 24437	—
Reactant	Methanesulfonamide	HCID 72879	—
Reactant	2-(1-Cyclohexenyl)-4,5-diphenyloxazole	HCID 18459139	—
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	—
Solvent	Water	HCID 962	—
Product	(1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane	HCID 57102465	—

Reaction Steps

A solution of AD-mix-α® (30 g) in a mixture of t-BuOH (600 ml) and water (600 ml) was stirred for 1 hour, and then methanesulfonamide (9.3 g) and 1-(4,5-diphenyloxazol-2-yl)-1-cyclohexene added to the solution at room temperature. After being stirred for 20 hours at the same temperature, sodium sulfite (60 g) was added, and the mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane (30 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06245790B1
Source dataset	uspto-grants-2001_06
ORD ID	ord-27b7ec55874c49e59f11a6abb4b69419
Source note	uspto-grants-2001_06