Phthalimide → Triphenylphosphine Oxide

HRID 1711200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711200
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9]O)([CH3:4])([CH3:3])[CH3:2].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[CH:29]1[CH:34]=[CH:33][C:32]([P:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:31][CH:30]=1.CC[O:50]C(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][N:22]1[C:18](=[O:28])[C:19]2[C:20](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:21]1=[O:23])([CH3:4])([CH3:3])[CH3:2].[C:36]1([P:35](=[O:50])([C:32]2[CH:31]=[CH:30][CH:29]=[CH:34][CH:33]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 7016461Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester

Produkt 2

HCID 13097Triphenylphosphine OxideHCID 68775880HCID 68775880, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. solution of the alcohol (4.75 g, 20.0 mmol), phthalimide (3.32 g, 22.6 mmol) and PPh3 (6.30 g, 24.0 mmol) in THF (130 ml) under nitrogen was added dropwise DEAD (3.3 ml, 21.0 mmol). The resulting light yellow solution was stirred at room temperature for 3 hours, and then the solvent was removed under reduced pressure, giving crude [(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-phenyl-ethyl]-carbamic acid tert-butyl ester as a mixture with triphenylphosphine oxide.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b785585f293f4b2b9947014b2ff1dcd3
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790747B2

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