Water → 2-benzyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

HRID 733224Notes

Reaction equation

HRID 733224 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>CO.[BH4-].[K+]>[OH:13][CH:12]1[C:11]2[C:10](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9](=[O:18])[N:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 75059Benzylphthalimide

Product 1

HCID 32407432-benzyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-oneYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

3-Hydroxy-2-benzyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 10.2 g of N-benzylphthalimide in 100 cm3 of methanol and 2.6 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 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 3 times with 50 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. 9.5 g of 3-hydroxy-2-benzyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder. (Rf=0.20, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 by volume)).

Workup

  1. custom3-Hydroxy-2-benzyl-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.
  4. additionfollowed by addition of a further 50 cm3 of distilled water
  5. extractionThe aqueous phase is extracted 3 times with 50 cm3 of ethyl acetate
  6. washwashed with 50 cm3 of brine
  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
  10. 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-d38d4753c0c347ec81733a984ad06f70
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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