1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-hydroxymethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol

HRID 1599126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599126
CN(C)CCCN=C=NCC.[OH:12][CH2:13][CH:14]1[CH2:22][CH:21]2[CH:17]([CH2:18][NH:19][CH2:20]2)[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])([OH:23])[CH2:15]1.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C@H:40]([CH3:44])[C:41](O)=[O:42]>ClCCl.O.OC1C2N=NNC=2C=CC=1>[OH:12][CH2:13][CH:14]1[CH2:22][CH:21]2[CH:17]([CH2:18][N:19]([C:41](=[O:42])[C@H:40]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[O:33][CH3:32])[CH3:44])[CH2:20]2)[C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])([OH:23])[CH2:15]1

Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11137716(S)-2-(2-Methoxyphenyl)propanoic acidHCID 67660910(3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol

Produkt 1

HCID 228722946-hydroxymethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-olAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178526939HCID 178526939, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

2.1 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide are added to a solution of 2.77 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol, 1.80 g of (S)-2-(2-methoxyphenyl)propionic acid and 30 mg of hydroxybenzotriazole hydrate in 80 cm3 of dichloromethane. After stirring at 20° C. for 20 hours, the reaction mixture is washed with 40 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.06-0.20 mm, height 40 cm) in a mixture of cyclohexane and ethyl acetate (30:70 by volume) and then in a mixture of ethyl acetate and methanol (90:10 by volume). Evaporation of the eluent and drying. I under reduced pressure (2.7 kPa) give 3.6 g of 6-hydroxymethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol (mixture of the 2 diastereoisomers, 3aR,4R,6S,7aS,S and 3aS,4S,6R,7aR, S) in the form of a white solid. M.p.K =178° C.

Aufarbeitung

  1. washthe reaction mixture is washed with 40 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed on a silica gel column (particle size 0.06-0.20 mm, height 40 cm) in a mixture of cyclohexane and ethyl acetate (30:70 by volume)
  5. additionin a mixture of ethyl acetate and methanol (90:10 by volume)
  6. customEvaporation of the eluent
  7. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-b51a30563a0542b7914d272d6bb7b457
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739351

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