Stannous chloride dihydrate → 1-Benzyl-4-(3,4-dichlorophenyl)pyrrolidin-3-amine

HRID 910429Notes

Reaction equation

HRID 910429 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([N+:13]([O-])=O)[CH:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[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[CH2:9][CH:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH:11]([NH2:13])[CH2:12]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 67025719(3SR,4RS)-1-Benzyl-3-(3,4-dichloro-phenyl)-4-nitro-pyrrolidine

Product 1

HCID 672341221-Benzyl-4-(3,4-dichlorophenyl)pyrrolidin-3-amineYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (3SR,4RS)-1-benzyl-3-(3,4-dichloro-phenyl)-4-nitro-pyrrolidine (15.0 g, 0.0427 mol) in EtOAc (200 ml) was added portionwise SnCl2.2H2O (43.36 g, 0.192 mol). The reaction mixture was then heated at reflux for 4 hours, cooled down to RT and a saturated aqueous solution of NaHCO3 (500 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 9.30 g (75%) of the title compound as a light yellow oil. The product was then used in the next step without further purification. ES-MS m/e: 321.1 (M+H+).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 4 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-a088ef0513424887951407cd3ac85ed3
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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