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4-Toluenesulfonyl chloride → (3aS,4S,6R,7aR)-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]-6-tosyloxymethyl perhydroisoindol-4-ol

HRID 1599125
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1599125
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH:14]1[CH2:22][CH:21]2[CH:17]([CH2:18][N:19]([C:23](=[O:34])[C@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])[CH3:25])[CH2:20]2)[C:16]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[O:42][CH3:43])([OH:35])[CH2:15]1.C(N(CC)CC)C>ClCCl>[CH3:43][O:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[C@:16]1([OH:35])[CH2:15][C@H:14]([CH2:13][O:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:22][C@@H:21]2[C@H:17]1[CH2:18][N:19]([C:23](=[O:34])[C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][CH3:33])[CH3:25])[CH2:20]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 228722946-hydroxymethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol

Produkt 1

HCID 22884866(3aS,4S,6R,7aR)-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]-6-tosyloxymethyl perhydroisoindol-4-olAusbeute 20,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

20.1 g of p-toluenesulphonyl chloride are added to a solution of 23.2 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) and 14.9 cm3 of triethylamine in 300 cm3 of dichloromethane. After stirring at 20° C. for 48 hours, the reaction mixture is washed with 150 cm3 of water, then 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, diameter 8.0 cm, height 45 cm), eluting under a pressure of 0.8 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50:50 by volume) and collecting fractions of 500 cm3. Fractions 14 to 17 are concentrated to dryness under reduced pressure. The residue obtained is subsequently chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 7.5 cm, height 60 cm), eluting under a pressure of 0.8 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60:40 then 50:50 by volume) and collecting fractions of 500 cm3. Evaporation to dryness of fractions 22 to 26 gives 6.5 g of the (3aS,4S,6R,7aR)-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]-6-tosyloxymethyl perhydroisoindol-4-ol diastereoisomer in the form of a thick white foam.

Aufarbeitung

  1. washthe reaction mixture is washed with 150 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, diameter 8.0 cm, height 45 cm)
  5. washeluting under a pressure of 0.8 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50:50 by volume)
  6. customcollecting fractions of 500 cm3
  7. concentrationFractions 14 to 17 are concentrated to dryness under reduced pressure
  8. customThe residue obtained
  9. customis subsequently chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 7.5 cm, height 60 cm)
  10. washeluting under a pressure of 0.8 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (60:40
  11. custom50:50 by volume) and collecting fractions of 500 cm3
  12. customEvaporation to dryness of fractions 22 to 26

Quellen und Nachweise

ORD-Eintrag
ord-1fc42ecd8b2448389dcb8b19336007a2
Quelldatensatz
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05739351

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