HCID 7571206, compound → HCID 17966416, compound

HRID 733254Notes

Reaction equation

HRID 733254 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6](=[O:7])[C:5]2=[CH:15][C:16]=1[Cl:17]>CO.[BH4-].[K+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:15][C:16]=1[Cl:17])[C:6](=[O:7])[N:8]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH:9]2[OH:10]

Participants

4

Reactant 1

HCID 7571206HCID 7571206, compound

Product 1

HCID 17966416HCID 17966416, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4192641Potassium borohydrideSolvent

Conditions

Temperature
20 °C

Procedure

5,6-Dichloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 3.78 g of 4,5-dichloro-N-isobutylphthalimide in 75 cm3 of methanol and 0.75 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours and is then cooled to a temperature in the region of 0° C. and distilled water is 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 100 cm3 of ethyl acetate. After separation of the phases by settling, the aqueous phase is extracted twice with 75 cm3 of ethyl acetate. The organic extracts are combined, washed with 150 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. 3.42 g of 5,6-dichloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are thus obtained in the form of an off-white solid. (Rf=0.69, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

Workup

  1. custom5,6-Dichloro-3-hydroxy-2-isobutyl-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 methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C.
  6. additionfollowed by addition of 100 cm3 of ethyl acetate
  7. customAfter separation of the phases
  8. extractionthe aqueous phase is extracted twice with 75 cm3 of ethyl acetate
  9. washwashed with 150 cm3 of brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-587a7140301244e38bc4eaad2e022858
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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