Triethylamine → 3-(4-Nitro-1-oxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

HRID 1883586Notes

Reaction equation

HRID 1883586 reaction equation
[O:1]=[C:2]1[CH:7]([NH:8][C:9]([O:11]CC2C=CC=CC=2)=O)[CH2:6][CH:5]([O:19][C:20](=[O:22])[CH3:21])[C:4](=[O:23])[NH:3]1.C(N(CC)CC)C.Br[CH2:32][C:33]1[C:42]([N+:43]([O-:45])=[O:44])=[CH:41][CH:40]=[CH:39][C:34]=1C(OC)=O>C(O)(=O)C.CN(C)C=O.[Pd]>[N+:43]([C:42]1[CH:41]=[CH:40][CH:39]=[C:34]2[C:33]=1[CH2:32][N:8]([CH:7]1[CH2:6][CH:5]([O:19][C:20](=[O:22])[CH3:21])[C:4](=[O:23])[NH:3][C:2]1=[O:1])[C:9]2=[O:11])([O-:45])=[O:44]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateHCID 12047333HCID 12047333, compound

Product 1

HCID 222411953-(4-Nitro-1-oxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,6-dioxo-3-benzyloxycarbonylamino-5-acetoxypiperidine (9 g, 28.2 mmol) and Pd/C (10%, 0.9 g) in acetic acid (90 mL) is shaken under hydrogen (50-60 psi) for 3 hours. The suspension is filtered through a pad of Celite and washed with acetic acid and the solvent is then removed in vacuo. The residue, triethylamine (2.9 g, 28 mmol), and methyl 2-bromomethyl-3-nitrobenzoate (7.7 g, 28.2 mmol) in dimethylformamide (100 mL) is heated at 80° C. for 18 hours. The solvent is removed in vacuo to give 3-(4-nitro-1-oxoisoindolin-2-yl)-2,6-dioxo-5-acetoxy-piperidine which can be further purified by column chromatography.

Workup

  1. filtrationThe suspension is filtered through a pad of Celite
  2. washwashed with acetic acid
  3. customthe solvent is then removed in vacuo
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-0968f0f8ec334b5b9d66d45d9abb79a7
Source dataset
uspto-grants-2004_07
Patent number
US06762195B2

Reaction notes

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