tert-butyl(+)-cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-ethanoate → (+)-Cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}ethanoic Acid

HRID 877229Notes

Reaction equation

HRID 877229 reaction equation
[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]3=[O:30])=[CH:16][CH:15]=2)[C:7]([O:9]C(C)(C)C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]3=[O:30])=[CH:16][CH:15]=2)[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 58074501tert-butyl(+)-cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-ethanoate

Product 1

HCID 58074558(+)-Cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}ethanoic Acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

At RT, 695 mg (1.71 mmol) of tert-butyl(+/−)-cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate were dissolved in 11 ml of a 4 N solution of hydrogen chloride in dioxane, and the mixture was stirred for 12 h. The reaction mixture was then frozen and freeze-dried under high vacuum. This gave 700 mg of product, which was not purified any further.

Workup

  1. temperatureThe reaction mixture was then frozen
  2. customfreeze-dried under high vacuum
  3. customThis gave 700 mg of product, which was not purified any further

Sources & evidence

ORD record
ord-df11f8d4c8f24f719252b22abb7179cd
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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