HCID 90110274, compound → HCID 118037366, compound

HRID 1508771Notes

Reaction equation

HRID 1508771 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][CH:9]([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(OCC)(=O)C.CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[C:16]([O:18][CH:19]([CH3:20])[CH3:21])=[O:17])=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 90110274HCID 90110274, compound

Product 1

HCID 118037366HCID 118037366, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A 100-mL round bottom flask was charged with diisopropyl 2-(4-nitrobenzyl)malonate (1.19 g, 3.68 mmol) and 10% palladium on carbon (0.30 g) in 1:1 ethyl acetate/methanol (20 mL). This mixture was vigorously stirred under H2 (1 atm) for 2.5 h. After this time, the mixture was filtered through celite and purified by chromatography on silica eluting with hexanes/ethyl acetate (10:1 to 0:10) to afford the title compound (0.34 g, 32%) as a white solid. MW=293.36. 1H NMR (DMSO-d6, 500 MHz) δ 6.83 (d, J=7.5 Hz, 2H), 6.44 (d, J=7.0 Hz, 2H), 4.91-4.82 (m, 4H), 3.55 (t, J=8.0 Hz, 1H), 2.86 (d, J=8.0 Hz, 2H), 1.14 (d, J=6.0 Hz, 6H), 1.11 (d, J=8.0 Hz, 6H).

Workup

  1. filtrationAfter this time, the mixture was filtered through celite
  2. custompurified by chromatography on silica eluting with hexanes/ethyl acetate (10:1 to 0:10)

Sources & evidence

ORD record
ord-8475e6539f07410e9f4eeed6f098047e
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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