HCID 68898935, compound → HCID 131727754, compound

HRID 1435928Notes

Reaction equation

HRID 1435928 reaction equation
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=2[N+:21]([O-])=O)[C:10]([C:29](OCC)=[O:30])([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:20][O:19][C:15]1[C:14]2[NH:21][C:29](=[O:30])[C@:10]3([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:9][NH:8][CH2:12][C@@H:11]3[C:13]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 68898935HCID 68898935, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131727754HCID 131727754, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of diethyl 1-benzyl-4-(3-methoxy-2-nitrophenyl)pyrrolidine-3,3-dicarboxylate (200 mg, 0.44 mmol) in 20 mL of methanol was added 10% Pd/C catalyst (40 mg, 20% by wt). The mixture was placed on a Parr shaker under 50 psi of hydrogen for 18 h. The reaction was filtered through a pad of Celite and concentrated in vacuo. The residue was purified by flash chromatography (elution with 5% methanol/methylene chloride) to afford 77 mg (60%) of the title compound as a solid. LRMS (ESI): 291.2 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (elution with 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-9bb8e793350746ec8a157dc4bc9df1e7
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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