Triphenylphosphine → 2-Azido-4-methyl-cyclohexanecarboxylic acid ethyl ester

HRID 1807977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807977
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][CH:7]1O)=[O:5])[CH3:2].C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][CH:7]1[N:28]=[N+:29]=[N-:30])=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15227139HCID 15227139, Verbindung

Produkt 1

HCID 597523872-Azido-4-methyl-cyclohexanecarboxylic acid ethyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Hydroxy-4-methyl-cyclohexanecarboxylic acid ethyl ester (495 mg, 2.66 mmol) was dissolved in THF (13 ml) and then diphenylphosphoryl azide (680 ul, 3.19 mmol) and triphenylphosphine (837 mg, 3.19 mmol) were added. The resulting solution was cooled in an ice bath and diethyl azodicarboxylate (502 ul, 3.19 mmol) was added. After stirring at room temperature for 20 hours, the solvents were removed and the residue was purified by flash chromatography (0% to 3% EtOAc/Hexane) to obtain 365 mg (65%) of 2-Azido-4-methyl-cyclohexanecarboxylic acid ethyl ester.

Aufarbeitung

  1. temperatureThe resulting solution was cooled in an ice bath
  2. customthe solvents were removed
  3. customthe residue was purified by flash chromatography (0% to 3% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f18ddd2cff51418899f58d560e50f756
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357718B2

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