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

HRID 733246
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HRID 733246 반응식
[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]
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참가 물질

5

반응물 2

HCID 962WaterHCID 22025411N-isobutyl-4-isopropyloxyphthalimide

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 4192641Potassium borohydride용매

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온도
20 °C

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-8427d63f9c574142a0cfeecc48bd92b8
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07589117B2

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