4-(2-methoxycarbonylthiophen-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester → 4-(2-Methoxycarbonylthiophen-3-yl)piperidine-1-carboxylic acid t-butyl ester

HRID 41642

Reaktionsgleichung

Reaktionsgleichung von HRID 41642
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:18]=[CH:17][S:16][C:15]=2[C:19]([O:21][CH3:22])=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][S:16][C:15]=2[C:19]([O:21][CH3:22])=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 584428134-(2-methoxycarbonylthiophen-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 584428354-(2-Methoxycarbonylthiophen-3-yl)piperidine-1-carboxylic acid t-butyl esterAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4-(2-methoxycarbonylthiophen-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (2.5 g, 7.7 mmol, 1.0 eq.) and Pd(OH)2/C (0.5 g, 0.6 mmol) in MeOH (70 mL) was degassed and purged with hydrogen (3×). The mixture was hydrogenated (4 atm) at room temperature overnight, then the vessel was evacuated and purged with nitrogen, and the material was filtered and washed with MeOH (150 mL). The remaining material was concentrated then again was hydrogenated (4 atm) at room temperature overnight. Filtering again as above, and concentrating the filtrate provided 4-(2-methoxycarbonylthiophen-3-yl)piperidine-1-carboxylic acid t-butyl ester (2.4 g).

Aufarbeitung

  1. custompurged with hydrogen (3×)
  2. customat room temperature
  3. customovernight
  4. customthe vessel was evacuated
  5. custompurged with nitrogen
  6. filtrationthe material was filtered
  7. washwashed with MeOH (150 mL)
  8. concentrationThe remaining material was concentrated
  9. customat room temperature
  10. customovernight
  11. filtrationFiltering again as above, and
  12. concentrationconcentrating the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-4cf72d806fa54367b63badc338672e7d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530663B2

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