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

HRID 55402

반응식

HRID 55402 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.C([O:14][CH:15]1[CH2:23][CH2:22][CH:21]2[CH:17]([CH2:18][N:19]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20]2)[C:16]1=[O:31])(=O)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH2:24]([N:19]1[CH2:18][CH:17]2[CH:21]([CH2:22][CH2:23][CH:15]([OH:14])[C:16]2([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[OH:31])[CH2:20]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 67714196(3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindoloneHCID 178489560HCID 178489560, 화합물

생성물 1

HCID 67713929(3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol수율 26.8%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of 27.6 g of 2-methoxyphenylmagnesium bromide in 60 cm' of tetrahydrofuran are added dropwise, at room temperature and with stirring, a solution of 4.7 g of (3aRS,5RS,7aSR)-5-acetoxy-2-benzyl-4-perhydroisoindolone in 90 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 3 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution and taken up in 200 cm3 of ethyl ether and 100 g of ice. The organic phase is separated out after settling has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 80 cm3 of petroleum ether and then chromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 20 cm), eluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (95/5 by volume) and collecting 25 cm3 fractions. Fractions 14 to 21 are combined and then concentrated to dryness under reduced pressure (2.5 kPa). 1.55 g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 140° C.

후처리

  1. additionare added dropwise, at room temperature
  2. stirringThe reaction mixture is stirred at room temperature for 3 hours
  3. customThe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallized in 80 cm3 of petroleum ether
  8. customchromatographed on a column of silica gel (particle size 0.04-0.06 mm, diameter 1 cm, height 20 cm)
  9. washeluting under a pressure of 0.5 bar of nitrogen with a mixture of dichloromethane and methanol (95/5 by volume)
  10. customcollecting 25 cm3 fractions
  11. concentrationconcentrated to dryness under reduced pressure (2.5 kPa)

출처 및 근거

ORD 기록
ord-67d3926d58e94c3b98873508a730e72e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624950

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