Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate → HCID 58975237, compound

HRID 1178880Notes

Reaction equation

HRID 1178880 reaction equation
[CH3:1][CH2:2][O:3][C:4]([N:6]1[CH:10]2[CH2:11][C:12]([CH2:14][CH:7]1[CH2:8][CH2:9]2)=O)=[O:5].[Cl-].[CH3:16][O:17][CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[CH3:16][O:17][CH:18]=[C:12]1[CH2:14][CH:7]2[N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:10]([CH2:9][CH2:8]2)[CH2:11]1

Participants

5

Reactant 3

HCID 401882Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 58975237HCID 58975237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-carbethoxy-4-tropinone (1-1) (8.00 g, 40.6 mmol, Acros) and (methoxymethyl)tripheylphosphonium chloride (16.7 g, 48.7 mmol) in THF was added sodium bis(trimethylsilyl)amide (48.7 mL, 48.7 mmol, 1.0 N in THF) at 0° C. After stirring at room temperature overnight, the solvent was removed by rotary evaporation. The mixture was quenched with a saturated aqueous solution of NH4Cl, extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-20% ethyl acetate/hexanes as eluent) afforded (1-2) as a colorless oil.

Workup

  1. customthe solvent was removed by rotary evaporation
  2. customThe mixture was quenched with a saturated aqueous solution of NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude residue
  9. customPurification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-20% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-0f8cc83a94f34744970be34dce9bf0c1
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

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