2-Methoxy-beta-nitrostyrene → (1R,2R,3R,4S)-ethyl 4-((ethoxycarbonyl)methyl)-1-acetyl-2-(2-methoxyphenyl)-3-nitro-cyclopentanecarboxylate

HRID 407524Notes

Reaction equation

HRID 407524 reaction equation
[C:1]([CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:5][CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:2].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1/[CH:26]=[CH:27]/[N+:28]([O-:30])=[O:29]>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][CH3:17])=[O:14])[C@@H:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][CH3:18])[C@@H:27]1[N+:28]([O-:30])=[O:29])=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 7106692-Methoxy-beta-nitrostyreneHCID 85439255Diethyl 5-acetylhex-2-enedioate

Product 1

HCID 59592077(1R,2R,3R,4S)-ethyl 4-((ethoxycarbonyl)methyl)-1-acetyl-2-(2-methoxyphenyl)-3-nitro-cyclopentanecarboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of diethyl 5-acetylhex-2-enedioate (4a, 0.3 mmol, 1.0 eq) and 1-methoxy-2-((E)-2-nitrovinyl)benzene (0.6 mmol, 2.0 eq) in diethyl ether (0.4 mL) was added catalyst VI (Q-NH2) (0.06 mmol, 0.2 eq) at room temperature (22° C.). The resulting mixture was stirred vigorously for 24 hours, 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 1:3) in 81% yield.

Workup

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

Sources & evidence

ORD record
ord-d85ea5aeb6fd4aa48e2a754fed1e899c
Source dataset
uspto-grants-2014_06
Patent number
US08754252B2

Reaction notes

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