Triethylamine → HCID 22843242, Verbindung

HRID 1029919

Reaktionsgleichung

Reaktionsgleichung von HRID 1029919
[C:1]1([C@@H:7]([CH3:11])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:13]1([C:19]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:27]3[C@H:23]([CH2:24][NH:25][CH2:26]3)[C:22](=[O:28])[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[C:29]1([C:19]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:27]3[C@H:23]([CH2:24][N:25]([C:8](=[O:10])[C@@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH3:11])[CH2:26]3)[C:22](=[O:28])[CH2:21][CH2:20]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 4466262-Phenylpropionic acid, (-)-HCID 22843247(3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride

Produkt 1

HCID 22843242HCID 22843242, VerbindungAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N,N'-Carbonyldiimidazole (0.66 g) is added to a solution of (R)-2-phenylpropionic acid (0.62 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 30 minutes at +5° C. and a solution of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (1.35 g) and triethylamine (0.57 cc) in dichloromethane (40 cc) is then added. The reaction mixture is stirred at 20° C. for 16 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in ethyl acetate (100 cc) and the solution is washed with water (2×50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (4 kPa). The residue is chromatographed on a silica gel column (0.2-0.04 mm, diameter 2.8 cm, height 15 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (60/40 by volume) and collecting 50 cc fractions. Fractions 4 to 8 are concentrated to dryness under reduced pressure (4 kPa) to give (3aR,7aR)-7,7-diphenyl-2-[(R)-2-phenylpropionyl]-4-perhydroisoindolone (1.4 g) in the form of a white meringue, the infrared spectrum of which is identical to that of the product from Example 68; [α]D20 =-278° (c=1, methanol).

Aufarbeitung

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred at 20° C. for 16 hours
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. dissolutionThe residue is dissolved in ethyl acetate (100 cc)
  5. washthe solution is washed with water (2×50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated to dryness under reduced pressure (4 kPa)
  9. customThe residue is chromatographed on a silica gel column (0.2-0.04 mm, diameter 2.8 cm, height 15 cm)
  10. washeluting under a nitrogen pressure of 0.5 bar
  11. additionwith a mixture of cyclohexane and ethyl acetate (60/40 by volume)
  12. customcollecting 50 cc fractions
  13. concentrationFractions 4 to 8 are concentrated to dryness under reduced pressure (4 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-a605b45fa2c846f697314a8ae2ed8040
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

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