N-Isopropylphthalimide → HCID 11629744, compound

HRID 733218Notes

Reaction equation

HRID 733218 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])([CH3:3])[CH3:2]>CO.[BH4-].[K+]>[OH:9][CH:8]1[C:7]2[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:14])[N:4]1[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67535N-Isopropylphthalimide

Product 1

HCID 11629744HCID 11629744, compoundYield 150.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

3-Hydroxy-2-isopropyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 4.0 g of N-isopropylphthalimide in 20 cm3 of methanol and 1.1 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 distilled water is added dropwise. The solvent is then evaporated to dryness under reduced pressure (2 kPa) at a temperature in the region of 35° C. 6.1 g of 3-hydroxy-2-isopropyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white wax. (Rf=0.65, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (30/70 by volume)).

Workup

  1. custom3-Hydroxy-2-isopropyl-2,3-dihydroisoindol-1-one is prepared
  2. temperatureis then cooled to a temperature in the region of 0° C.
  3. distillationdistilled water
  4. additionis added dropwise
  5. customThe solvent is then evaporated to dryness under reduced pressure (2 kPa) at a temperature in the region of 35° C

Sources & evidence

ORD record
ord-b88a54f2682e4406801172d8aa423779
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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