Trifluoroacetic acid → 5-(1-Methylethoxy)-6-nitro-2-(4-piperidinyl)-1H-isoindole-1,3(2H)-dione

HRID 1946892Notes

Reaction equation

HRID 1946892 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][C:18]([N+:28]([O-:30])=[O:29])=[C:19]([O:24][CH:25]([CH3:27])[CH3:26])[CH:20]=3)[C:15]2=[O:31])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:25]([O:24][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[N+:28]([O-:30])=[O:29])[C:15](=[O:31])[N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:22]2=[O:23])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67071138HCID 67071138, compound

Product 1

HCID 670710975-(1-Methylethoxy)-6-nitro-2-(4-piperidinyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-isopropoxy-6-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester generated in the previous step in 3 mL of DCM is added TFA (3 mL). The reaction mixture is stirred at room temperature for 1 h. After concentration, water (5 mL) is added to the crude reaction mixture, the resulting mixture is neutralized to pH=8 by adding NaHCO3, and the product is extracted with DCM. The organic extracts are dried over Na2SO4, filtered and concentrated in vacuo to give crude 5-isopropoxy-6-nitro-2-piperidin-4-yl-isoindole-1,3-dione, which is directly used in the next step without further purification.

Workup

  1. concentrationAfter concentration, water (5 mL)
  2. additionis added to the crude
  3. customreaction mixture
  4. extractionthe product is extracted with DCM
  5. dry with materialThe organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8eb6f5f15eb4850866eb58a4c4b6b8b
Source dataset
uspto-grants-2013_03
Patent number
US08399450B2

Reaction notes

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