1-Nitro-4-phenylbutadiene → (1R,2R,3R,4S)-benzyl 4-((ethoxycarbonyl)methyl)-1-acetyl-3-nitro-2-styrylcyclopentanecarboxylate

HRID 407527Notes

Reaction equation

HRID 407527 reaction equation
[C:1]([CH:4]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:5][CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:2].[N+:23](/[CH:26]=[CH:27]/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([O-:25])=[O:24]>C(OCC)C>[CH2:11]([O:10][C:8]([CH2:7][C@@H:6]1[CH2:5][C@@:4]([C:1](=[O:3])[CH3:2])([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C@@H:27]([CH:28]=[CH:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@@H:26]1[N+:23]([O-:25])=[O:24])=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 64401831-Nitro-4-phenylbutadieneHCID 687750396-Benzyl 1-ethyl 5-acetylhex-2-enedioate

Product 1

HCID 86648074(1R,2R,3R,4S)-benzyl 4-((ethoxycarbonyl)methyl)-1-acetyl-3-nitro-2-styrylcyclopentanecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-benzyl 1-ethyl 5-acetylhex-2-enedioate (4b, 0.3 mmol, 1.0 eq) and 1-((1E,3E)-4-nitrobuta-1,3-dienyl)benzene (0.6 mmol, 2.0 eq) in diethyl ether (0.4 mL) was added catalyst VI (Q-NH2) (0.03 mmol, 0.2 eq) at room temperature (22° C.). The resulting mixture was stirred vigorously for 24 hours, and then the reaction was continued for about 6 hours after removal of the solvent. After the reaction was completed (monitored by TLC and crude NMR), the title product was afforded by flash chromatography over silica gel (Et2O:Hexane=1:10 to 1:4) in 83% yield.

Workup

  1. waitthe reaction was continued for about 6 hours
  2. customafter removal of the solvent

Sources & evidence

ORD record
ord-bd5e200ed802432490f3e342747d7f16
Source dataset
uspto-grants-2014_06
Patent number
US08754252B2

Reaction notes

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