Methanol → 1-Azabicyclo[3.2.2]nonan-4-one

HRID 2176083Notes

Reaction equation

HRID 2176083 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.CCCCCC.[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C:16](=[O:22])[CH2:15]2.CO>O1CCCC1>[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C:16](=[O:22])[CH2:15][CH2:1]2

Participants

5

Reactant 3

HCID 887MethanolHCID 195073-QuinuclidinoneHCID 86587183Trimethylsilyldiazomethane hexane

Product 1

HCID 64203071-Azabicyclo[3.2.2]nonan-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ice-cooled solution (5° C.) of (trimethylsilyl)diazomethane/hexane (2 N, 30 mL, 60 mmol; Aldrich) under nitrogen was treated dropwise with a solution of quinuclidin-3-one (7500 mg, 60 mmol) in dry tetrahydrofuran (40 mL). Methanol (20 mL) was added, and the yellow solution was warmed to room temperature, stirred for 24 hours, and quenched to colorless by addition of acetic acid. After a few minutes, saturated aqueous sodium carbonate (15 mL) was added. The organic layer was separated, and the aqueous solution was extracted with methylene chloride (3×50 mL). The combined organic layer and extracts were dried over magnesium sulfate, and concentrated in vacuo to give the titled compound. The material was used directly for next step without further purification.

Workup

  1. customquenched
  2. additionto colorless by addition of acetic acid
  3. waitAfter a few minutes
  4. additionsaturated aqueous sodium carbonate (15 mL) was added
  5. customThe organic layer was separated
  6. extractionthe aqueous solution was extracted with methylene chloride (3×50 mL)
  7. dry with materialThe combined organic layer and extracts were dried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b244a81a2cdc48d384ff7d3cfe27f4dd
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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