(3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol → (3aRS,4RS,5RS,7aSR)-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol

HRID 55401노트

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HRID 55401 반응식
C([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH2:12][CH:13]([OH:26])[C:14]2([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[OH:17])[CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:14]1([OH:17])[CH:13]([OH:26])[CH2:12][CH2:11][CH:10]2[CH:15]1[CH2:16][NH:8][CH2:9]2

참가 물질

4

반응물 1

HCID 67713929(3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol

생성물 1

HCID 67714228(3aRS,4RS,5RS,7aSR)-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol수율 91.3%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

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온도
60 °C

실험 절차

A mixture of 1.5 g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol and 120 cm3 of anhydrous ethanol is heated to 60° C. with stirring; 0.49 g of 20% palladium hydroxide on charcoal is added and the reaction mixture is then hydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure. After reaction for 2 hours, the theoretical volume of hydrogen has been absorbed; the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 50 cm3 of isopropyl ether. 1.02 g of (3aRS,4RS,5RS,7aSR)-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 168° C.

후처리

  1. stirringhydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure
  2. customAfter reaction for 2 hours
  3. customthe theoretical volume of hydrogen has been absorbed
  4. filtrationthe reaction mixture is filtered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized in 50 cm3 of isopropyl ether

출처 및 근거

ORD 기록
ord-4d899db9016443ecad44fc47bd05fcb1
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624950

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