N-Hydroxyphthalimide → HCID 22861110, Verbindung

HRID 439893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 439893
N(C(OCC)=O)=NC(OCC)=O.[C:13]([NH:20][CH2:21][C@H:22]1[CH2:24][C@H:23]1[CH2:25][OH:26])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O[N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[C:13]([NH:20][CH2:21][C@H:22]1[CH2:24][C@H:23]1[CH2:25][O:26][N:28]1[C:32](=[O:33])[C:31]2[C:30](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]1=[O:38])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Komponenten

6

Edukt 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11820138tert-butyl cis-N-[[(1S,2R)-2-(hydroxymethyl)cyclopropyl]methyl]carbamate

Produkt 1

HCID 22861110HCID 22861110, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

A solution of 2.61 ml (0.0157 mol) of diethyl azodicarboxylate (93%) in 15 ml of benzene is added dropwise to a mixture of 3 g (0.0149 mol) of cis-2-(N-BOC-aminomethyl)-cyclopropanemethanol, 2.43 g (0.0149 mol) of N-hydroxyphthalimide, 3.9 g (0.0149 mol) of triphenylphosphine and 120 ml of benzene at 20°-30° C., while stirring. The reaction mixture is stirred at room temperature for 16 hours and filtered, the crystalline residue is washed with benzene and the filtrate is evaporated in vacuo. The residue is purified by means of flash chromatography on silica gel using hexane and hexane/ethyl acetate (2:1). After evaporation of the product-containing fractions and crystallization of the residue from methanol/hexane, the title compound is obtained, m.p. 96°-97° C.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at room temperature for 16 hours
  2. filtrationfiltered
  3. washthe crystalline residue is washed with benzene
  4. customthe filtrate is evaporated in vacuo
  5. customThe residue is purified by means of flash chromatography on silica gel
  6. customAfter evaporation of the product-containing fractions and crystallization of the residue from methanol/hexane

Quellen und Nachweise

ORD-Eintrag
ord-5d6b424caee3460888f1785817ac7572
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516806

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