Stannous Chloride → HCID 57494449, compound

HRID 1260265Notes

Reaction equation

HRID 1260265 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([O:22][CH3:23])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)Cl>CO>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([O:22][CH3:23])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 574700891-Benzyl-3-(3-methoxy-4-nitro-phenyl)-pyrrolidine

Product 1

HCID 57494449HCID 57494449, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-3-(3-methoxy-4-nitro-phenyl)-pyrrolidine (350 mg, 1.12 mmol) was dissolved in methanol (20 ml), tin dichloride (1.912 g, 10.08 mmol) was added, and the reaction mixture stirred at reflux for 2 h. The methanol was evaporated, 1 N sodium hydroxide (50 ml) and ethyl acetate were added and stirring continued. The tin salts were filtered off, the organic phase was separated, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield an oil (220 mg, 70%).

Workup

  1. temperatureat reflux for 2 h
  2. customThe methanol was evaporated
  3. addition1 N sodium hydroxide (50 ml) and ethyl acetate were added
  4. stirringstirring
  5. filtrationThe tin salts were filtered off
  6. customthe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-48553bec0bad4b84beebc58091c5258a
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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