Phthalimide → HCID 58951233, Verbindung

HRID 46156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46156
N(C(OCC)=O)=NC(OCC)=O.[Si:13]([O:30][C@H:31]1[CH2:36][C@H:35]2[CH2:37][C@@H:32]1[CH2:33][C@H:34]2O)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Si:13]([O:30][C@H:31]1[CH2:36][C@H:35]2[CH2:37][C@@H:32]1[CH2:33][C@@H:34]2[N:43]1[C:39](=[O:49])[C:40]2[C:41](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:42]1=[O:44])([C:26]([CH3:29])([CH3:27])[CH3:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58951276HCID 58951276, Verbindung

Produkt 1

HCID 58951233HCID 58951233, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of diethyl azodicarboxylate (2.58 mL, 16.4 mmol) in anhydrous THF (10.0 mL) was added dropwise to a mixture of (1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)bicyclo[2.2.1 ]heptan-2-ol (5.00 g, 13.6 mmol), phthalimide (2.31 g, 15.7 mmol), and triphenyl phosphine (4.11 g, 15.7 mmol) in anhydrous THF (60 mL) at ambient temp. under nitrogen. After stirring for 32 h, the solvents were removed in vacuo. The residue was purified by flash column chromatography (0 to 20% of ethyl acetate in hexanes) to give the title compound as a white solid. MS m/z: 496.3 (M+H)+.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. customThe residue was purified by flash column chromatography (0 to 20% of ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e885f66e12f2415b96407ce14b0df5c9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541592B2

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