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Allyltrimethylsilane → tert-butyl [7-(hepta-1,6-dien-4-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate

HRID 511492
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 511492
C(O[CH:5]([C:9]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:14]2[C:10]=1[CH2:11][N:12]([CH3:27])[C:13]2=[O:26])[CH2:6][CH:7]=[CH2:8])(=O)C.[Br-].[Br-].[Br-].[In+3].[CH2:32]([Si](C)(C)C)[CH:33]=[CH2:34]>C(Cl)Cl>[CH2:8]=[CH:7][CH2:6][CH:5]([C:9]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[C:14]2[C:10]=1[CH2:11][N:12]([CH3:27])[C:13]2=[O:26])[CH2:34][CH:33]=[CH2:32]
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Komponenten

5

Edukt 3

HCID 69808AllyltrimethylsilaneHCID 167051indium(III)bromideHCID 672543181-{7-[(tert-butoxycarbonyl)amino]-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl}but-3-en-1-yl acetate2×

Produkt 1

HCID 58293015tert-butyl [7-(hepta-1,6-dien-4-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 1-{7-[(tert-butoxycarbonyl)amino]-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl}but-3-en-1-yl acetate (Compound 243E, 895 mg, 2.39 mmol) in DCM (30 mL) were added indium tribromide (85 mg, 0.24 mmol), followed by the addition of allyltrimethylsilane (550 mg, 4.8 mmol) in DCM (0.5 mL). The resulting mixture was refluxed under nitrogen overnight. The solvent was evaporated and the residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-50% EtOAc/Heptane) to give the desired product as a white solid, 180 mg. The unreacted starting material was recovered and resubjected to the reaction using 2.0 eq. allyltrimethylsilane and 0.2 eq. InBr3. The mixture was refluxed overnight. The solvent was evaporated and the residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-50% EtOAc/Heptane) to give the desired product as a white solid, 125 mg. Totally 305 mg, 36% yield. 1H NMR (CDCl3): 1.53 (s, 9H), 2.34-2.47 (m, 4H), 2.67 (m, 1H), 3.16 (s, 3H), 4.27 (s, 2H), 4.92-4.99 (m, 4H), 5.55-5.64 (m, 2H), 7.29 (d, J=8.6 Hz, 1H), 8.16 (d, J=8.6 Hz, 1H), 9.52 (br s, 1H). MS (ES+): m/z=379.13 [MNa+]. HPLC: tR=4.83 min (ZQ3, polar—5 min).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed under nitrogen overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography (ISCO Combi-flash system, eluting with 10-50% EtOAc/Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-ee33992c6e21426ba5cc15fff6cd7a77
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096624B2

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