4,4'-(1-(4-tert-butylphenyl)pyrrolidine-2,5-diyl)bis(N-(4-methoxybenzyl)-2-nitroaniline) → 4,4'-(1-(4-tert-butylphenyl)pyrrolidine-2,5-diyl)bis(N1-(4-methoxybenzyl)benzene-1,2-diamine)

HRID 1411424Notes

Reaction equation

HRID 1411424 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:31]=[CH:30][C:19]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[C:18]([N+:32]([O-])=O)[CH:17]=3)[CH2:14][CH2:13][CH:12]2[C:35]2[CH:50]=[CH:49][C:38]([NH:39][CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=3)=[C:37]([N+:51]([O-])=O)[CH:36]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.C(O)C.C(OCC)(=O)C.[Pt]=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:12]([C:35]3[CH:36]=[C:37]([NH2:51])[C:38]([NH:39][CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=4)=[CH:49][CH:50]=3)[CH2:13][CH2:14][CH:15]2[C:16]2[CH:17]=[C:18]([NH2:32])[C:19]([NH:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)=[CH:30][CH:31]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 1

HCID 866491004,4'-(1-(4-tert-butylphenyl)pyrrolidine-2,5-diyl)bis(N-(4-methoxybenzyl)-2-nitroaniline)

Product 1

HCID 666307194,4'-(1-(4-tert-butylphenyl)pyrrolidine-2,5-diyl)bis(N1-(4-methoxybenzyl)benzene-1,2-diamine)Yield 28%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4,4′-(1-(4-tert-Butylphenyl)pyrrolidine-2,5-diyl)bis(N-(4-methoxybenzyl)-2-nitroaniline) (2 g, 2.79 mmol) was dissolved in a mixture of THF (15 mL), ethanol (15 mL), and ethyl acetate (5 mL). Then platinum oxide (0.254 g, 1.12 mmol) was added as a THF slurry. The flask was evacuated and purged with nitrogen twice, then evacuated and opened to a hydrogen balloon. The mixture was stirred at room temperature for 20 hours, then filtered through diatomaceous earth, concentrated, and purified by chromatography on silica gel with an 80 g column, eluting with 0-40% ethyl acetate/dichloromethane to give the first peak of trans product (0.508 g, 28%).

Workup

  1. customThe flask was evacuated
  2. custompurged with nitrogen twice
  3. customevacuated
  4. filtrationfiltered through diatomaceous earth
  5. concentrationconcentrated
  6. custompurified by chromatography on silica gel with an 80 g column
  7. washeluting with 0-40% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-ecbcd0a56f7344f58da9d5138b3d6672
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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