Hydrochloric Acid → HCID 68734622, compound

HRID 2382197Notes

Reaction equation

HRID 2382197 reaction equation
C[C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.C([N:23]1[CH2:27][CH2:26][C:25](=O)[CH2:24]1)(OC(C)(C)C)=O.Cl.[CH2:30]1COCC1>[Zn].Cl[Ti](Cl)(Cl)Cl>[C:6]1(/[C:4](/[C:3]2[CH:2]=[C:15]([CH3:30])[CH:14]=[CH:13][CH:12]=2)=[C:25]2/[CH2:24][NH:23][CH2:27][CH2:26]/2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 672302-MethylbenzophenoneHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 68734622HCID 68734622, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalyst

Procedure

To a mixture of 2-methylbenzophenone (2.0 g, 10.2 mmol) and N-boc-3-pyrrolidone (1.89 g, 10.2 mmol) in THF was added zinc powder (3.3 g, 59 mmol) at 10-15° C. and stirred for 15 min. To the reaction mixture was added TiCl4 (4.76 g, 25 mmol) and the contents were brought to 60° C. and stirred for 8 h. The reaction mixture was allowed to cool to room temperature, diluted HCl was added and extracted with EtOAc. The organic layer was washed with aqueous sodium potassium tartarate solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product which was washed with n-hexane to afford 1.8 g of (Z)-3-(phenyl(m-tolyl)methylene)pyrrolidine.

Workup

  1. customwere brought to 60° C.
  2. stirringstirred for 8 h
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with aqueous sodium potassium tartarate solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product which
  8. washwas washed with n-hexane

Sources & evidence

ORD record
ord-7a5174dae521469d92dfd45be9741812
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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