Phthalimide → Triphenylphosphine Oxide

HRID 60812

Reaktionsgleichung

Reaktionsgleichung von HRID 60812
C[CH:2]([O:4]C(/N=N/C(OC(C)C)=O)=O)C.[C:15]1(C2C=CC=CC=2)[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([N:23]1[CH:28]=[C:27]([O:29][CH3:30])[CH2:26][CH2:25][CH:24]1[CH2:31]O)=[O:22].[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.[CH:50]1[CH:55]=[CH:54][C:53]([P:56]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[CH:52][CH:51]=1>C1COCC1>[C:15]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:16]([C:21]([N:23]2[CH2:28][C:27]([O:4][CH3:2])([O:29][CH3:30])[CH2:26][CH2:25][CH:24]2[CH2:31][N:43]2[C:39](=[O:49])[C:40]3[C:41](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:42]2=[O:44])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=1.[C:57]1([P:56](=[O:4])([C:53]2[CH:52]=[CH:51][CH:50]=[CH:55][CH:54]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 117728177biphenyl-2-yl(2-(hydroxymethyl)-5-methoxy-3,4-dihydropyridin-1 (2H)-yl)methanone

Produkt 2

HCID 13097Triphenylphosphine OxideHCID 897395602-((1-(Biphenylcarbonyl)-5,5-dimethoxypiperidin-2-yl)methyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DIAD (15.15 mmol, 2.93 mL) was added to a mixture of (biphenyl-2-yl(2-(hydroxymethyl)-5-methoxy-3,4-dihydropyridin-1 (2H)-yl)methanone (4.5 mmol, 1.63 g), phthalimide (15.15 mmol, 2.23 g) and PPh3 (15.15 mmol, 3.97 g) in anhydrous THF dropwise at 0° C. under argon. The resulting mixture was stirred at rt for overnight and concentrated in vacuo to give a crude residue which was purified by chromatography to give the desired 2-((1-(biphenylcarbonyl)-5,5-dimethoxypiperidin-2-yl)methyl)isoindoline-1,3-dione with slight contamination of triphenylphosphine oxide. This contaminated product was used for next step without further purification.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto give a crude residue which
  3. customwas purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d92f4215d53f47aeba8c81a8470c2de7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440982B2

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