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

HRID 733246Notes

Reaction equation

HRID 733246 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2=[CH:11][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=[C:7]2[C:6]1=[O:19])[CH:2]([CH3:4])[CH3:3].O>CO.[BH4-].[K+]>[CH:16]([O:15][C:12]1[CH:11]=[C:8]2[C:7](=[CH:14][CH:13]=1)[C:6](=[O:19])[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH:9]2[OH:10])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 962WaterHCID 22025411N-isobutyl-4-isopropyloxyphthalimide

Product 1

HCID 220254425-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-oneYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

5-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 1.16 g of N-isobutyl-4-isopropyloxyphthalimide in 20 cm3 of methanol and 0.24 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 17 hours and then cooled to a temperature in the region of 0° C. and 30 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., and 50 cm3 of water are added. The aqueous phase is extracted 3 times with 70 cm3 of ethyl acetate. The organic extracts are combined, washed with 100 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. 1.08 g of 5-isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a viscous colorless oil. (Rf=0.50, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

Workup

  1. custom5-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared
  2. additionare added dropwise
  3. customThe methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C., and 50 cm3 of water
  4. additionare added
  5. extractionThe aqueous phase is extracted 3 times with 70 cm3 of ethyl acetate
  6. washwashed with 100 cm3 of saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-8427d63f9c574142a0cfeecc48bd92b8
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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