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

HRID 1850923Notes

Reaction equation

HRID 1850923 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-737a899ecb8049f28ec12ebea7393a45
Source dataset
uspto-grants-2015_02
Patent number
US08957081B2

Reaction notes

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