Hydrochloric Acid → 1-(4-Tert-butylphenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

HRID 1470934Notes

Reaction equation

HRID 1470934 reaction equation
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[C:33]([C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1)([CH3:36])([CH3:35])[CH3:34].C(OCC)(=O)C.Cl>CN(C=O)C>[C:33]([C:37]1[CH:38]=[CH:39][C:40]([N:41]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH:6]2[C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[CH:42][CH:43]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 698614-Tert-ButylanilineHCID 596171791,4-Bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 873789961-(4-Tert-butylphenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 1C (3.67 g, 7.51 mmol) and 4-tert-butylaniline (11.86 ml, 75 mmol) in DMF (40 ml) was stirred under nitrogen at 50° C. for 4 h. The resulting mixture was diluted into ethyl acetate, treated with 1M HCl, stirred for 10 minutes and filtered to remove solids. The filtrate organic layer was washed twice with brine, dried with sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with ethyl acetate in hexane (5% to 30%) to give a solid. The solid was triturated in a minimal volume of 1:9 ethyl acetate/hexane to give a light yellow solid as a mixture of trans and cis isomers (1.21 g, 36%).

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. washThe filtrate organic layer was washed twice with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate in hexane (5% to 30%)
  8. customto give a solid
  9. customThe solid was triturated in a minimal volume of 1:9 ethyl acetate/hexane
  10. customto give a light yellow solid
  11. additionas a mixture of trans and cis isomers (1.21 g, 36%)

Sources & evidence

ORD record
ord-7898ff5637f64860afc0434a78d0f6cb
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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