Triphenylphosphine → HCID 66999426, Verbindung

HRID 559295

Reaktionsgleichung

Reaktionsgleichung von HRID 559295
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[N:25][CH:26]=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.[CH2:50]([N:57]1[CH2:61][C@H:60]([C:62]2[CH:67]=[CH:66][C:65]([Cl:68])=[CH:64][CH:63]=2)[C@@H:59]([C@H:69](O)[CH3:70])[CH2:58]1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1COCC1>[CH2:50]([N:57]1[CH2:61][C@H:60]([C:62]2[CH:63]=[CH:64][C:65]([Cl:68])=[CH:66][CH:67]=2)[C@@H:59]([C@@H:69]([O:27][C:24]2[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][N:25]=2)[CH3:70])[CH2:58]1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 66999400HCID 66999400, VerbindungHCID 1785160645-chloropyridin-2-ol

Produkt 1

HCID 66999426HCID 66999426, VerbindungAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (0.44 g, 1.69 mmol) in THF (50 mL) at 0° C. were added 5-chloro-pyridin-2-ol (0.15 g, 1.15 mmol) and then DBAD (0.28 g, 1.23 mmol). After 5 minutes was added (R)-1-[(3R,4S)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethanol (0.25 g, 0.79 mmol). The reaction mixture was stirred over night at RT, filtered on celite and concentrated under vacuo. Extraction with EtOAc/aq.NaOH 1M, followed by column chromatography (SiO2, EtOAc/H, 1:3) yielded 0.22 g (65%) of the title compound as a colorless oil. ES-MS m/e: 427.8 (M+H+).

Aufarbeitung

  1. filtrationfiltered on celite
  2. concentrationconcentrated under vacuo
  3. extractionExtraction with EtOAc/aq

Quellen und Nachweise

ORD-Eintrag
ord-89ae718251e14922bfe3195e4722fff2
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063075B2

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