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 1470927Notes

Reaction equation

HRID 1470927 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

The product from Example 28E (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 via THF slurry. The flask was evacuated and purged with nitrogen twice, then evacuated and opened to hydrogen balloon. The mixture was stirred at room temperature for 20 h, then filtered through celite, 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 celite,
  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-05788c17f52b47eb88af0dfec33e503a
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

Loading…