Sodium Methoxide → (+)-9-(3-Bromo-4-fluorophenyl)-2,3,5,9-tetrahydro-4h-pyrano[3,4-b]thieno[2,3-e]pyridin-8(7h)-one 1,1-dioxide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Methoxide	HCID 10942334	—
Reactant	(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-(3-bromo-4-fluorophenyl)-8-oxo-2,3,5,7,8,9-hexahydro-4H-pyrano[3,4-b]thieno[2,3-e]pyridine-4-carboxylate 1,1-dioxide	HCID 69303668	—
Catalyst	Methanol	HCID 887	—
Solvent	Dichloromethane methanol	HCID 21226129	—
Product	(+)-9-(3-Bromo-4-fluorophenyl)-2,3,5,9-tetrahydro-4h-pyrano[3,4-b]thieno[2,3-e]pyridin-8(7h)-one 1,1-dioxide	HCID 9887983	62.1%

Reaction Steps

A solution of Example 12A (0.98 g, 1.4 mmol) in methanol/methylene chloride (40 mL/10 mL) was degassed with nitrogen, treated with of 25% sodium methoxide in methanol (30 drops), stirred for 16 hours, filtered, and concentrated to a volume of 5 mL of methanol. The solid which had precipitated was collected by filtration, washed with methanol and dried under vacuum for 16 hours to provide the title compound (0.36 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06642222B2
Source dataset	uspto-grants-2003_11
ORD ID	ord-2037307b69f54b9b81ce3effeabd3f80
Source note	uspto-grants-2003_11