(S)-1-Benzyl-3-(3-nitro-phenyl)-pyrrolidine → (S)-1-Benzyl-3-(3-amino-phenyl)-pyrrolidine

HRID 238969Notes

Reaction equation

HRID 238969 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 68948946(S)-1-Benzyl-3-(3-nitro-phenyl)-pyrrolidine

Product 1

HCID 68954497(S)-1-Benzyl-3-(3-amino-phenyl)-pyrrolidineYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-Benzyl-3-(3-nitro-phenyl)-pyrrolidine (1 g, 3.54 mmol) was dissolved in methanol, 4.5 g of stannous dichloride (19.94 mmol) were added and the reaction mixture was stirred for 1.5 h under refluxing conditions. When the starting material was consumed, the solvent was evaporated under reduced pressure and the residue treated with a mixture of 1 N aqueous NaOH/ethyl acetate and filtered over celite. Phases were separated, the aqueous phase was extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, filtered and evaporated to dryness to yield 0.75 g of a yellowish oil.

Workup

  1. customWhen the starting material was consumed
  2. customthe solvent was evaporated under reduced pressure
  3. additionthe residue treated with a mixture of 1 N aqueous NaOH/ethyl acetate
  4. filtrationfiltered over celite
  5. customPhases were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. dry with materialthe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-49dd995230444bb68f94facdd1f8d05c
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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