Triphenylphosphine → 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-dichloronitrobenzene

HRID 1268224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268224
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([Cl:25])[C:17]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:17]2[C:18]([Cl:25])=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=2[Cl:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 120662,6-Dichloro-4-nitrophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 185426044-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3,5-dichloronitrobenzeneAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (677 mg), 2,6-dichloro-4-nitrophenol (700 mg) and triphenylphosphine (1150 mg) in dichloromethane (40 ml) was added dropwise diethyl azodicarboxylate (0.67 ml) in an ice bath and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=6/1 as an eluant to give the desired compound (950 mg, yield 72%) as a colorless solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-58ca57e0caa8443f854973a92ec00d16
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555556B1

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