Toluene → HCID 178469205, Verbindung

HRID 525472

Reaktionsgleichung

Reaktionsgleichung von HRID 525472
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:23])[CH:19]=3)[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:24]1([CH:30]2[CH2:35][CH2:34][CH:33](O)[CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:24]1([C@@H:30]2[CH2:35][CH2:34][C@H:33]([O:23][C:18]3[CH:19]=[C:20]4[C:15](=[CH:16][CH:17]=3)[CH:14]=[C:13]([CH2:12][N:9]3[CH2:10][CH2:11][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]3)[CH:22]=[CH:21]4)[CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 794974-PhenylcyclohexanolHCID 68279222Ethyl 1-((6-hydroxynaphthalen-2-yl)methyl)piperidine-4-carboxylate

Produkt 1

HCID 178469205HCID 178469205, VerbindungAusbeute 50 %

Versuchsvorschrift

A mixture of 1-(6-hydroxy-naphthalen-2-ylmethyl)-piperidine-4-carboxylic acid ethyl ester (0.400 g, 1.28 mmol), 4-phenyl-cyclohexanol (0.2479 g, 1.406 mmol) and triphenylphosphine (0.6695 g, 2.553 mmol) in toluene (5 mL, 40 mmol) was stirred for 20 min, then diisopropyl azodicarboxylate (0.32 mL, 1.5 mmol) was added dropwise at 0° C. The solution was stirred at reflux overnight. The reaction was added silica gel and the solvent was concentrated. The residue was purified with silica gel eluted with EtOAc in hexanes from 0 to 20% to give product as an oil (0.3 g, 50%). LCMS: Rt=1.75 min, m/z=472.45 [M+H].

Aufarbeitung

  1. stirringThe solution was stirred
  2. temperatureat reflux overnight
  3. additionThe reaction was added silica gel
  4. concentrationthe solvent was concentrated
  5. customThe residue was purified with silica gel
  6. washeluted with EtOAc in hexanes from 0 to 20%

Quellen und Nachweise

ORD-Eintrag
ord-5f1015eb4a024fe496a210a4adf75146
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340527B2

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