Phthalimide → HCID 54366715, Verbindung

HRID 617173

Reaktionsgleichung

Reaktionsgleichung von HRID 617173
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][CH2:16]/[C:17](=[CH:18]\[CH:19]=[C:20]3\[CH2:21][C@@H:22](O)[CH2:23][CH2:24][C:25]\3=[CH2:26])/[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:29]1(=[O:39])[N:33]([CH:22]2[CH2:23][CH2:24][C@@:25]3([CH3:26])[CH:20]([CH2:19][CH2:18][C@@H:17]4[C@@H:16]3[CH2:15][CH2:14][C@@:13]3([CH3:28])[C@H:12]4[CH2:11][CH2:10][C@@H:9]3[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:21]2)[C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5280795Vitamin D3HCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 54366715HCID 54366715, VerbindungAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of dihydrocholesterol (5.0 g, 12.9 mmol, Aldrich), phthalimide (2.0 g, 13.6 mmol, Aldrich), and triphenylphosphine (3.8 g, 13.6 mmol, Aldrich) in THF (20 ml, Aldrich) stirred at 0° C. under a nitrogen atmosphere was added dropwise diethylazodicarboxylate (2.3 ml, 14.5 mmol, Aldrich). Upon the completion of addition the reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was concentrated in vacuo to a residue. This residue was dissolved in 50 ml hexane/ethyl acetate 95/5 and a precipitate formed. The mixture was filtered. The filtrate was concentrated to dryness in vacuo, dissolved in 25 ml of hexane/ethyl acetate 95/5 and chromatographed on 200 g silica gel (eluent 2 L hexane/ethyl acetate 95/5 then 1 L hexane/ethyl acetate 90/10). A 76% yield of the desired 3-phthalimidocholestane (5.43 g) was obtained.

Aufarbeitung

  1. additionUpon the completion of addition the reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo to a residue
  3. dissolutionThis residue was dissolved in 50 ml hexane/ethyl acetate 95/5
  4. customa precipitate formed
  5. filtrationThe mixture was filtered
  6. concentrationThe filtrate was concentrated to dryness in vacuo
  7. dissolutiondissolved in 25 ml of hexane/ethyl acetate 95/5
  8. customchromatographed on 200 g silica gel (eluent 2 L hexane/ethyl acetate 95/5

Quellen und Nachweise

ORD-Eintrag
ord-d34a53e513174f30acf321e8e5e6101f
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948767

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