Diethyl Ether → Methyl 5-(4-piperidyl)pentanoate

HRID 257738

Reaktionsgleichung

Reaktionsgleichung von HRID 257738
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17](O)=O)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C[CH2:21][O:22][CH2:23]C.S(Cl)(Cl)=[O:26].[N+](=C)=[N-]>N1C=CC=CC=1.CO.C([O-])(=O)C1C=CC=CC=1.[Ag+].CCN(CC)CC>[NH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:21]([O:22][CH3:23])=[O:26])[CH2:12][CH2:13]1

Komponenten

9

Edukt 4

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 24386Thionyl ChlorideHCID 104009874-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)butanoic acid

Produkt 1

HCID 19781432Methyl 5-(4-piperidyl)pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1049PyridineKatalysatorHCID 164649Silver benzoateKatalysatorHCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of carboxylic acid 14 (600 mg, 2.2 mmol), ether (4.0 mL), and pyridine (2 drops) at ambient temperature was added thionyl chloride in one portion to effect an exotherm. After 25 minutes the ether, pyridine, and thionyl chloride were evaporated. The intermediate acid chloride was dissolved in ether (5 mL), cooled to 0° C., then treated with an ethereal solution of diazomethane (15 mL, ~10 mmol). After 2.0 hours the excess diazomethane was removed by purging with argon. Evaporation in situ gave a solid that was dissolved in CH3OH (10 mL) then treated sequentially with NEt3 (0.5 mL) and silver benzoate (20 mg). After 15 minutes the black reaction mixture was concentrated and the residue subjected to flash chromatography (silica, 10% ethyl acetate/hexanes) to give 15 (300 mg) as an oil.

Aufarbeitung

  1. customAfter 25 minutes the ether, pyridine, and thionyl chloride were evaporated
  2. dissolutionThe intermediate acid chloride was dissolved in ether (5 mL)
  3. customAfter 2.0 hours the excess diazomethane was removed
  4. customby purging with argon
  5. customEvaporation in situ
  6. customgave a solid
  7. concentrationAfter 15 minutes the black reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-30a5365b4045493d9954ed939f26fbab
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264420

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