Acetic Acid → Ethyl 1-methylpiperidine-4-carboxylate

HRID 238438

Reaktionsgleichung

Reaktionsgleichung von HRID 238438
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C=O.[C:14](O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH3:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 70770Ethyl 4-piperidinecarboxylateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 11062856Ethyl 1-methylpiperidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Piperidine-4-carboxylic acid ethyl ester (78 g) was dissolved in MeOH (1.2 L) at RT then formaldehyde (37%, 90 ml) and acetic acid (42 ml) were added and stirred for 2 h. The mixture was cooled to 0° C., NaCNBH3 (70 g) was added, and the mix was stirred for 20 min at 0° C., then overnight at RT. The mixture was cooled to 0° C. then quenched with 6N NaOH. The mixture was concentrated in vacuo to an aqueous layer, which was extracted with EtOAc (4×), brine-washed, dried over Na2SO4, and concentrated in vacuo to provide 1-methylpiperidine-4-carboxylic acid ethyl ester.

Aufarbeitung

  1. stirringthe mix was stirred for 20 min at 0° C.
  2. customovernight
  3. customat RT
  4. temperatureThe mixture was cooled to 0° C.
  5. customthen quenched with 6N NaOH
  6. concentrationThe mixture was concentrated in vacuo to an aqueous layer, which
  7. extractionwas extracted with EtOAc (4×), brine-
  8. washwashed
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae163eb1c1314ee4bece2682b9f8d38c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642624B2

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