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 635978

Reaction equation

HRID 635978 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 through a 45 mm syringe filter 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 through a 45 mm syringe
  2. filtrationfilter
  3. concentrationconcentrated to a volume of 5 mL of methanol
  4. customThe solid which had precipitated
  5. filtrationwas collected by filtration
  6. washwashed with methanol
  7. customdried under vacuum for 16 hours

Sources & evidence

ORD record
ord-1732fe06a1d141a9867e722956426a68
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Linked notes

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