Indole-3-Acetic Acid → (3aRS,4RS,7aRS)-7,7-diphenyl-2-(3-indolylacetyl)-4-(2-methoxyphenyl)-perhydroisoindol-4-ol

HRID 375437노트

반응식

HRID 375437 반응식
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]([OH:25])=O)=[CH:14]1.Cl.[C:27]1([C:33]2([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:41]3[CH:37]([CH2:38][NH:39][CH2:40]3)[C:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[O:49][CH3:50])([OH:42])[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>ClCCl>[C:51]1([C:33]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:41]3[CH:37]([CH2:38][N:39]([C:23](=[O:25])[CH2:22][C:15]4[C:16]5[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=5)[NH:13][CH:14]=4)[CH2:40]3)[C:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[O:49][CH3:50])([OH:42])[CH2:35][CH2:34]2)[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

참가 물질

6

반응물 4

HCID 802Indole-3-Acetic AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 21264542(3aRS,4RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindol-4-ol hydrochloride

생성물 1

HCID 18994349(3aRS,4RS,7aRS)-7,7-diphenyl-2-(3-indolylacetyl)-4-(2-methoxyphenyl)-perhydroisoindol-4-ol수율 12.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

0.41 g of cabonyldiimidazole is added to a solution of 0.44 g of 3-indolylacetic acid in 20 cm3 of dry dichloromethane. The mixture is stirred at room temperature for 1 hour and a suspension of 1.1 g of (3aRS,4RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride in 25 cm3 of dry dichloromethane and then 0.7 cm3 of triethylamine are subsequently added in succession. The reaction mixture is stirred at room temperature for 24 hours, diluted with 100 cm3 of dichloromethane, washed with 100 cm3 of water (twice) and then with 100 cm3 of an aqueous saturated solution of sodium chloride, and is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 22 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (35/65 by volume) and collecting-fractions of 20 cm3. Fractions 7 to 8 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is triturated in diisopropylether. 0.17 g of (3aRS,4RS,7aRS)-7,7-diphenyl-2-(3-indolylacetyl)-4-(2-methoxyphenyl)perhydroisoindol-4-ol is obtained in the form of a white solid.

후처리

  1. stirringThe reaction mixture is stirred at room temperature for 24 hours
  2. washwashed with 100 cm3 of water (twice) and then with 100 cm3 of an aqueous saturated solution of sodium chloride
  3. dry with materialis dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 22 cm)
  6. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (35/65 by volume)
  7. customcollecting-fractions of 20 cm3
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customThe residue is triturated in diisopropylether

출처 및 근거

ORD 기록
ord-09a27edb425042e08d44760eb9c8fd90
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05484804

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