Water → 5-Tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one

HRID 733228Notes

Reaction equation

HRID 733228 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[O:13])[N:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:9](=[O:10])[C:8]2=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].O>CO.[BH4-].[K+]>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:18][CH:19]=1)[C:9](=[O:10])[N:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH:12]2[OH:13])([CH3:4])([CH3:3])[CH3:2].[C:1]([C:5]1[CH:6]=[C:7]2[C:8]([CH:9]([OH:10])[N:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:12]2=[O:13])=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 962WaterHCID 220254784-tert-butyl-N-isobutylphthalimide

Product 2

HCID 220254325-Tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-oneHCID 220254776-Tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

5-tert-Butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 10.4 g of 4-tert-butyl-N-isobutylphthalimide in 60 cm3 of methanol and 2.3 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 19 hours and is then cooled to a temperature in the region of 0° C. and 50 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., followed by addition of a further 50 cm3 of distilled water. The aqueous phase is extracted twice with 100 cm3 of ethyl acetate. The organic extracts are combined, washed with 50 cm3 of brine, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C. 9.9 g of a mixture of 5-tert-Butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a yellow foam (Rf=0.26 and 0.30 unassigned, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 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. additionfollowed by addition of a further 50 cm3 of distilled water
  4. extractionThe aqueous phase is extracted twice with 100 cm3 of ethyl acetate
  5. washwashed with 50 cm3 of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  9. customThe residue is dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-823c8c78010547e5bf1ec1a85b5453f6
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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