Water → HCID 22025460, compound

HRID 733242Notes

Reaction equation

HRID 733242 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]2[C:10](=[O:11])[N:9]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:7](=[O:8])[C:6]2=[CH:16][CH:17]=1.O>CO.[BH4-].[K+]>[F:18][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]2[C:6]([CH:7]([OH:8])[N:9]([CH2:12][CH:13]([CH3:14])[CH3:15])[C:10]2=[O:11])=[CH:16][CH:17]=1.[F:18][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]2[C:6](=[CH:16][CH:17]=1)[C:7](=[O:8])[N:9]([CH2:12][CH:13]([CH3:14])[CH3:15])[CH:10]2[OH:11]

Participants

6

Reactant 2

HCID 962WaterHCID 22025506HCID 22025506, compound

Product 2

HCID 22025449HCID 22025449, compoundHCID 22025460HCID 22025460, compoundYield 160.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

5-Trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 14.9 g of 4-trifluoromethyl-N-isobutylphthalimide in 300 cm3 of methanol and 2.96 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours and then cooled to a temperature in the region of 0° C. and 100 cm3 of distilled water are added dropwise. The methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C. The aqueous phase is extracted 3 times with 200 cm3 of ethyl acetate. The organic extracts are combined, washed with 300 cm3 of saturated sodium chloride solution, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 12.07 g of 5-trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder. (Rf=0.64, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

Workup

  1. additionare added dropwise
  2. customThe methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. extractionThe aqueous phase is extracted 3 times with 200 cm3 of ethyl acetate
  4. washwashed with 300 cm3 of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-5945786f16fa463c9987db542dd50a87
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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