Chlorotrimethylsilane → 1-(8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)ethan-1-one

HRID 2226155Notes

Reaction equation

HRID 2226155 reaction equation
[C@@H:1]12[N:8]([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:10]([O:12]CC)=O.[Si](Cl)(C)(C)[CH3:16].[Li]C>C1COCC1>[CH3:9][N:8]1[CH:5]2[CH2:6][CH2:7][CH:1]1[C:2]([C:10](=[O:12])[CH3:16])=[CH:3][CH2:4]2

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 25222744Anhydroecgonine ethyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 5857561-(8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

To a mixture of ethyl trop-2-ene-2-carboxylate (3.43 g, 0.019 mol) and Me3SiCl (10.32 g, 0.095 mol) in THF (70 mL) cooled to -100° C., MeLi (1.4 M, 17.07 n%L, 0.0239 mol) was added dropwise. After warming up to room temperature, the reaction mixture was stirred for 16 hours. Excess Me3SiCl and THF was evaporated off and the resulting residue was stirred with EtOH (6 mL) followed by water (6 mL). The mixture was then made acidic (6N HCl )and extracted with ether. The aqueous layer was made basic (solid K2CO3)and extracted with chloroform, dried (K2CO3) and concentrated to give

Workup

  1. temperatureAfter warming up to room temperature
  2. customExcess Me3SiCl and THF was evaporated off
  3. stirringthe resulting residue was stirred with EtOH (6 mL)
  4. extractionmade acidic (6N HCl )and extracted with ether
  5. extractionextracted with chloroform
  6. dry with materialdried (K2CO3)
  7. concentrationconcentrated
  8. customto give

Sources & evidence

ORD record
ord-ae26fdafb80b4b869101bcd29f8dbee7
Source dataset
uspto-grants-1994_09
Patent number
US05346911

Reaction notes

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