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Triphenylphosphine → [4-(3-Amino-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-methanone

HRID 1794024
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1794024
[N:1]([CH:4]1[CH2:9][CH2:8][CH2:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH2:22][N:21]4[CH:29]=[CH:30][CH:31]=[C:20]4[CH2:19]3)=[O:17])=[CH:12][C:11]=2[CH3:32])=[C:5]1[CH3:33])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[NH2:1][CH:4]1[CH2:9][CH2:8][CH2:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH2:22][N:21]4[CH:29]=[CH:30][CH:31]=[C:20]4[CH2:19]3)=[O:17])=[CH:12][C:11]=2[CH3:32])=[C:5]1[CH3:33]
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Komponenten

5

Edukt 2

HCID 11776TriphenylphosphineHCID 10225076[4-(3-Azido-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone

Produkt 1

HCID 10158554[4-(3-Amino-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-methanoneAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[4-(3-Azido-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone of Step A (0.290 g, 0.663 mmol) was dissolved in 7 mL of a 10:1 mixture of tetrahydrofuran and water. Polymer-supported triphenylphosphine (0.287 g, approximately 0.862 mmol) was added and the reaction stirred at room temperature overnight. The mixture was filtered and concentrated, and the residue purified by flash column chromatography on silica gel, eluting with 3% ammonium hydroxide and 20% methanol in chloroform. A yellow oil was isolated which was triturated with 1:1 diethyl ether/petroleum ether to afford the title compound (0.100 g) as a white solid.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue purified by flash column chromatography on silica gel
  4. washeluting with 3% ammonium hydroxide and 20% methanol in chloroform
  5. customA yellow oil was isolated which
  6. customwas triturated with 1:1 diethyl ether/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-0d8f1473661a4019b460419498c3d008
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07022699B2

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