Triphenylphosphine → HCID 86708693, Verbindung

HRID 921796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921796
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[OH:27].[CH3:28][C:29]1([N:33]2[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]2)[CH2:32][O:31][CH2:30]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Cl:15][C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[O:27][CH:36]1[CH2:35][CH2:34][N:33]([C:29]2([CH3:28])[CH2:30][O:31][CH2:32]2)[CH2:38][CH2:37]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 23288677HCID 23288677, VerbindungHCID 86708694HCID 86708694, Verbindung

Produkt 1

HCID 86708693HCID 86708693, VerbindungAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DIAD (0.132 mL, 0.638 mmol) was added to a solution of 4-chloro-3-hydroxy-5-nitrobenzonitrile (95 mg, 0.478 mmol), 1-(3-methyloxetan-3-yl)piperidin-4-ol (78 mg, 0.456 mmol) and triphenylphosphine resin (3 mmol/g loading, 560 mg, 2.136 mrnmol) in THF (2 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (24 g column, eluting with 1-6% 2 N ammonia in methanol/dichloromethane). 4-chloro-3-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)-5-nitrobenzonitrile (106 mg) was obtained as a yellow solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe crude product was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (24 g column, eluting with 1-6% 2 N ammonia in methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-9d56a08fe77f4479b785f68e5b1fccb0
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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