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

HRID 373696

Reaktionsgleichung

Reaktionsgleichung von HRID 373696
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]([OH:10])=[O:9])[CH2:3]1.Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[CH2:22](N(CC)CC)C.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[CH2:15]([O:14][C:12]([N:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]([O:10][CH3:22])=[O:9])[CH2:3]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11957555Guvacine HydrochlorideHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 18797103Methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid, hydrochloride salt (1.8 g, 10 mmol) in methylene chloride (60 ml) was cooled to 0° C. Benzyl chloroformate (2.74 ml, 19.2 mmol) was added, followed by addition of triethylamine (7.2 ml, 51.2 mmol), and stirring at room temperature for 12 hours. The reaction mixture was washed with brine and dried over magnesium sulfate. Evaporation in vacuo afforded a yellow oil. This was purified by chromatography on silica gel (eluant: 20%, then 30% ethyl acetate/hexane) to give the product as a slightly yellow oil (2.14 g, 7.7 mmol, 77% yield).

Aufarbeitung

  1. washThe reaction mixture was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation in vacuo
  4. customafforded a yellow oil
  5. customThis was purified by chromatography on silica gel (eluant

Quellen und Nachweise

ORD-Eintrag
ord-c6c1ada189df4d508eeeb1fd1462ef93
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164402

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