N-Hydroxyphthalimide → 2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propoxy]isoindole-1,3-dione

HRID 78997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 78997
[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][C@@H:7]([CH3:10])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].O[N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][C@@H:7]([CH3:10])[CH2:8][O:9][N:14]1[C:18](=[O:19])[C:17]2[C:16](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]1=[O:24])([CH3:3])([CH3:4])[CH3:2]

Komponenten

6

Edukt 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 15688069(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propan-1-ol

Produkt 1

HCID 583743222-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propoxy]isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of (S)-2-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (53.0 g, 0.28 mol), N-hydroxyphthalimide (47.0 g, 0.29 mol) and triphenylphosphine (77.9 g, 0.30 mol) in THF (200 ml) at 0° C. was added dropwise DIAD (56.8 ml, 0.29 mol). During the addition the reagents dissolved and the solution turned a dark red colour before fading to pale yellow colour on completion of the addition. The reaction mixture was stirred and allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo and the resultant residue re-dissolved in diethyl ether. The suspension was filtered and the filtrate was concentrated in vacuo to yield the crude title compound as a pale yellow oil. The material was used without further purification in the subsequent step.

Aufarbeitung

  1. additionDuring the addition the reagents
  2. dissolutiondissolved
  3. additionbefore fading to pale yellow colour on completion of the addition
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe resultant residue re-dissolved in diethyl ether
  6. filtrationThe suspension was filtered
  7. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b60a2cb54444419c912959b2aecaceca
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841462B2

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