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Triphenylphosphine → t-Butyl 1,4-dioxepan-6-yl(1,3-dioxoisoindolin-2-yl)carbamate

HRID 1043881
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1043881
CCOC(/N=N/C(OCC)=O)=O.[O:13]1[CH2:19][CH:18](O)[CH2:17][O:16][CH2:15][CH2:14]1.[O:21]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[N:23]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:16]1[CH2:17][CH:18]([N:32]([N:23]2[C:22](=[O:21])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]2=[O:31])[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:19][O:13][CH2:14][CH2:15]1
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Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 801162N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(tert-butoxy)formamideHCID 5462977Diethyl azodicarboxylateHCID 137159861,4-Dioxepan-6-ol

Produkt 1

HCID 86686321t-Butyl 1,4-dioxepan-6-yl(1,3-dioxoisoindolin-2-yl)carbamateAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

DEAD (2.2 M in toluen, 1.55 mL) was added dropwise to a solution of 1,4-dioxepan-6-ol (265 mg), t-butyl (1,3-dioxoisoindolin-2-yl)carbamate (560 mg) obtained in preparation example 14-(1) and triphenylphosphine (840 mg) in THF (10 mL) under ice-cooling over 3 minutes. The reaction mixture was stirred at 0° C. for 6 minutes, and further stirred at room temperature overnight The reaction mixture was concentrated under reduced pressure. After toluene (2.5 mL) was added to the resulting residue, the precipitated solid was removed by filtration. The filtrate was purified by silica gel column chromatography (ethyl acetate/n-heptane, 20%) to give the title compound (713 mg).

Aufarbeitung

  1. stirringfurther stirred at room temperature overnight The reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additionAfter toluene (2.5 mL) was added to the resulting residue
  4. customthe precipitated solid was removed by filtration
  5. customThe filtrate was purified by silica gel column chromatography (ethyl acetate/n-heptane, 20%)

Quellen und Nachweise

ORD-Eintrag
ord-162a82999b05489ba8145a325ecca1d5
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563565B2

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