tert-Butanol → 3-(5-Fluoro-2-nitrophenoxy)cyclopentane-1,2-diol

Participants

Role	Name	HCID	Charge
Reactant	tert-Butanol	HCID 6386	—
Reactant	Sodium Pyrosulfite	HCID 656671	—
Reactant	HCID 19702686	HCID 19702686	—
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	3-(5-Fluoro-2-nitrophenoxy)cyclopentane-1,2-diol	HCID 58421488	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

AD-mix-alpha (7.57 g) was added to t-butanol (20.0 ml) and water (25.0 ml) and stirred for 10 min. The mixture was cooled to 0° C. and 2-(cyclopent-2-enyloxy)-4-fluoro-1-nitrobenzene (1.21 g) was added. After stirring at room temperature overnight the mixture was recooled at 0° C. and sodium metabisulfite (8.13 g) was added. After 10 min the reaction mixture was stirred at room temperature for 1 h and extracted with EtOAc. The combined organic extracts were washed with brine passed through a hydrophobic frit and concentrated in vacuo to yield the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08754079B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-f4192d23ba5346b48e24199f2341dce5
Source note	uspto-grants-2014_06