Pyrrolidine → 9-Methyl-3-(pyrrolidin-1-yl)-9-azabicyclo[3.3.1]non-3-ene

HRID 2354896Notes

Reaction equation

HRID 2354896 reaction equation
[CH3:1][N:2]1[C@@H:7]2[CH2:8][C:9]([CH2:11][C@H:3]1[CH2:4][CH2:5][CH2:6]2)=O.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[CH3:1][N:2]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][C:9]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[CH:11]2

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 6602484552-70-5

Product 1

HCID 596794649-Methyl-3-(pyrrolidin-1-yl)-9-azabicyclo[3.3.1]non-3-eneYield 100%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

To pseudo-pelletierine (1.5 g, 9.8 mmol) in toluene (75 mL) was added pyrrolidine (4.9 mL, 58.75 mmol). TiCl4 (0.66 mL, 6.0 mmol) in toluene (10 mL) was then added to the mixture at −5° C. The reaction mixture was left to warm up to rt and stirred for 2 days. The mixture was filtered and the filtrate was concentrated to a residue and toluene (100 mL) was added and the mixture was filtered again. The filtrate was concentrated to a residue to afford the product (2.0 g, 100%) as yellow oil.

Workup

  1. waitThe reaction mixture was left
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated to a residue and toluene (100 mL)
  4. additionwas added
  5. filtrationthe mixture was filtered again
  6. concentrationThe filtrate was concentrated to a residue

Sources & evidence

ORD record
ord-396bb454ba48485781ed7a32f8a1ce32
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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