Stannous chloride dihydrate → 1-Benzyl-4-phenylpyrrolidin-3-amine

HRID 1951065Notes

Reaction equation

HRID 1951065 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([N+:19]([O-])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([NH2:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 580091801-Benzyl-3-nitro-4-phenylpyrrolidine

Product 1

HCID 433170851-Benzyl-4-phenylpyrrolidin-3-amineYield 80.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of rac-(3S,4R)-1-benzyl-3-nitro-4-phenyl-pyrrolidine (1.0 g, 3.54 mmol) in EtOAc (50 ml) was added in one portion SnCl2.2H2O (3.99 g, 17.70 mmol). The reaction mixture was then heated at reflux for 2 hours, cooled down to RT and a saturated aqueous solution of NaHCO3 (100 ml) was added. The salts were filtered off and the product extracted with EtOAc. The organic phases were then dried over Na2SO4, and concentration under vacuum gave 0.72 g (80%) of rac-(3S,4R)-1-benzyl-4-phenyl-pyrrolidin-3-ylamine as a light yellow oil. The product was then used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe salts were filtered off
  4. extractionthe product extracted with EtOAc
  5. dry with materialThe organic phases were then dried over Na2SO4, and concentration under vacuum

Sources & evidence

ORD record
ord-48443375115841d6a4500be9c4f08eff
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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