Triphenylphosphine → 4-[3-(4-Methoxycarbonyl-2-methyl-phenoxy)-propyl]-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 220896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220896
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24](O)=[C:23]([CH3:28])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][O:17][C:24]2[CH:25]=[CH:26][C:21]([C:20]([O:19][CH3:18])=[O:29])=[CH:22][C:23]=2[CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylateHCID 5462977Diethyl azodicarboxylateHCID 11240684Methyl 4-hydroxy-3-methylbenzoate

Produkt 1

HCID 575553354-[3-(4-Methoxycarbonyl-2-methyl-phenoxy)-propyl]-piperidine-1-carboxylic Acid Tert-butyl EsterAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-(3-Hydroxy-propyl)-piperidine-1-carboxylic acid tert-butyl ester from Example E68.1 (400 mg, 1.64 mmol) and 4-hydroxy-3-methyl-benzoic acid methyl ester from Example E29 (274 mg, 1.64 mmol) were dissolved in THF (30 ml) and cooled down to 0° C. Polymer-supported triphenyl-phosphine (1.7 g, 2.46 mmol) then DEAD (0.387 ml, 2.46 mmol) were added and the mixture was heated at re-flux for 20 h. The resin was filtered off, washed with EtOAc and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; 20% EtOAC:80% cyclohexane) to yield the title compound (340 mg, 53%).

Aufarbeitung

  1. temperaturethe mixture was heated at re-flux for 20 h
  2. filtrationThe resin was filtered off
  3. washwashed with EtOAc
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; 20% EtOAC:80% cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-c5feb9ef99184824b65ed5daff4dd011
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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