methyl 1-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)piperidine-4-carboxylate → HCID 67254395, compound

HRID 511503Notes

Reaction equation

HRID 511503 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[C:5]([N+:21]([O-])=O)[CH:6]=[CH:7][C:8]=2[N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)[C:3]1=[O:24].[H][H]>CO.[Pd]>[NH2:21][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:15][CH2:16]2)=[C:9]2[C:4]=1[C:3](=[O:24])[N:2]([CH3:1])[CH2:10]2

Participants

5

Reactant 2

HCID 67255603methyl 1-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)piperidine-4-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 67254395HCID 67254395, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 1-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)piperidine-4-carboxylate (Compound 256B, 33 mg, 0.099 mmol) and palladium/C in methanol (1.0 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight. The reaction mixture was filtered through celite, concentrated in vacuo and used directly in next step without further purification (20 mg, 72% yield). MS (ES+): m/z 304.20 (100) [MH+]; HPLC: tR=0.58 min (UPLC, Analytical).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated in vacuo
  3. customused directly in next step without further purification (20 mg, 72% yield)

Sources & evidence

ORD record
ord-3c36e4c60ea148228d03fd56e43d3f73
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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