Triethylamine → Methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

HRID 1003381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003381
[NH:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1.C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl>[CH2:22]([O:21][C:19]([N:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 160492Guvacoline

Produkt 1

HCID 18797103Methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylateAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Arecoline (39.5 g, 0.25 mol) was dissolved in dry toluene (20 ml). 1-Chloroethyl chloroformate (30.5 ml) was added slowly at 0-5° C. The mixture was heated at 80° C. for 2 h, cooled to room temperature, filtered and evaporated to dryness in vacuo. The residue was dissolved in methylene chloride (400 ml) and extracted with 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to give methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (Yield: 30.5 g, 85%). Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (1.1 g, 7.8 mmol) was dissolved in methylene chloride (20 ml) and cooled to -15° C. Triethyl amine (2.2 ml, 15,8 mmol) and a solution of benzyl chloroformate (1.2 ml, 8,4 mmol) in methylene chloride (10 ml) were added. Stirring at room temperature for 1.5 h followed by evaporation to dryness. The residue was dissolved in methylene chloride and extracted with water two times. The organic layer separated, dried and evaporated to dryness in vacuo to give methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate as an oil (Yield: 2.0 g, 92%).

Aufarbeitung

  1. customfollowed by evaporation to dryness
  2. dissolutionThe residue was dissolved in methylene chloride
  3. extractionextracted with water two times
  4. customThe organic layer separated
  5. customdried
  6. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e6c5a213837f49e0a9ee6917641ff2e9
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046214

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