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-butanol (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 stirring the mixture 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 EtOAc and water. The organic layer was washed with 1N-hydrochloric acid solution, saturated sodium hydrogencarbonate and brine, dried over magnesium sulfate 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	US06437146B1
Source dataset	uspto-grants-2002_08
ORD ID	ord-fd34953ddac64e40aeb8c91e3cad3453
Source note	uspto-grants-2002_08