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

HRID 1792918노트

반응식

HRID 1792918 반응식
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[O:13])[N:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:9](=[O:10])[C:8]2=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].O>CO.[BH4-].[K+]>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:18][CH:19]=1)[C:9](=[O:10])[N:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH:12]2[OH:13])([CH3:4])([CH3:3])[CH3:2].[C:1]([C:5]1[CH:6]=[C:7]2[C:8]([CH:9]([OH:10])[N:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:12]2=[O:13])=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 962WaterHCID 220254784-tert-butyl-N-isobutylphthalimide

생성물 2

HCID 220254325-Tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-oneHCID 220254776-Tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 4192641Potassium borohydride용매

반응 조건

온도
20 °C

실험 절차

5-tert-Butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 10.4 g of 4-tert-butyl-N-isobutylphthalimide in 60 cm3 of methanol and 2.3 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 19 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 twice with 100 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. 9.9 g of a mixture of 5-tert-Butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a yellow foam (Rf=0.26 and 0.30 unassigned, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 by volume)).

후처리

  1. additionare added dropwise
  2. customThe methanol is then partially evaporated off under reduced pressure (2 kPa) at a temperature in the region of 40° C.
  3. additionfollowed by addition of a further 50 cm3 of distilled water
  4. extractionThe aqueous phase is extracted twice with 100 cm3 of ethyl acetate
  5. washwashed with 50 cm3 of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  9. customThe residue is dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

출처 및 근거

ORD 기록
ord-4ae975eb7c3f4dfbbf156b0a5ec3ab12
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078428B2

반응 노트

불러오는 중…