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

HRID 478268

Reaction equation

HRID 478268 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[S:15](=[O:19])(=[O:18])[CH2:16][CH2:17][C:13]=3[N:12](C(O[C@@H]3C[C@H](C)CC[C@H]3C(C)(C3C=CC=CC=3)C)=O)[C:11]3[CH2:39][O:40][CH2:41][C:42](=[O:43])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].C[O-].[Na+]>CO.C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[S:15](=[O:18])(=[O:19])[CH2:16][CH2:17][C:13]=3[NH:12][C:11]3[CH2:39][O:40][CH2:41][C:42](=[O:43])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 69303668(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

Product 1

HCID 9887983(+)-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-dioxideYield 62.1%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

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).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to a volume of 5 mL of methanol
  3. customThe solid which had precipitated
  4. filtrationwas collected by filtration
  5. washwashed with methanol
  6. customdried under vacuum for 16 hours

Sources & evidence

ORD record
ord-2037307b69f54b9b81ce3effeabd3f80
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Linked notes

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