Methanol → HCID 18461088, compound

HRID 2303338Notes

Reaction equation

HRID 2303338 reaction equation
P([O-])([O-])(O)=O.[Na+].[Na+].CO.[CH2:10]1[O:37][C:13]2([CH2:19][CH2:18][CH:17]3[N:20]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:14]2[CH2:15][CH:16]3S(C2C=CC=CC=2)(=O)=O)[O:12][CH2:11]1>O1CCCC1.[Na].[Hg]>[CH2:11]1[O:12][C:13]2([CH2:19][CH2:18][CH:17]3[N:20]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:14]2[CH2:15][CH2:16]3)[O:37][CH2:10]1

Participants

6

Reactant 3

HCID 887MethanolHCID 24203Sodium Phosphate, DibasicHCID 18461089HCID 18461089, compound

Product 1

HCID 18461088HCID 18461088, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in Synth. Commun., 25:3681-3690 (1995) to prepare the analogous 8-methyl compounds was used. In a three-neck flask equipped with a thermometer, an argon inlet, and a powder funnel were placed sodium hydrogenphosphate (dibasic) (7.10g, 50.0 mmol), and dry methanol (8 mL). A solution of (±)-6-benzenesulfonyl-8-benzyl-8-aza-bicyclo[3.2.1]octan-2-one ethylene acetal (J. Heterocyclic Chem., 34:1139-1146(1997) (2.00 g, 5.0 mmol) in tetrahydrofuran (16 mL) was added. Sodium mercury amalgam (20% sodium) (5 g) was added portionwise with stirring at such a rate as to keep the temperature below 50° C. The mixture was stirred an additional 1.5 h at ambient temperature. The organic solution was decanted away from the inorganic residue. The inorganic residue was washed with tetrahydrofuran (3×8 mL). The combined organic portion was concentrated under reduced pressure. The residue was dissolved in water (32 mL) and extracted with dichloromethane (4×16 mL). The combined extract was washed with brine (20 mL), dried (sodium sulfate), filtered, and the solvent was evaporated under reduced pressure to give crude product (1.21 g, 89%) as an oil.

Workup

  1. customIn a three-neck flask equipped with a thermometer, an argon inlet, and a powder funnel
  2. customthe temperature below 50° C
  3. stirringThe mixture was stirred an additional 1.5 h at ambient temperature
  4. customThe organic solution was decanted away from the inorganic residue
  5. washThe inorganic residue was washed with tetrahydrofuran (3×8 mL)
  6. concentrationThe combined organic portion was concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in water (32 mL)
  8. extractionextracted with dichloromethane (4×16 mL)
  9. extractionThe combined extract
  10. washwas washed with brine (20 mL)
  11. dry with materialdried (sodium sulfate)
  12. filtrationfiltered
  13. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f8c8ab65dc5349b2a3fed4daaed5260d
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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