Hydrochloric Acid → Methyl-2-dimethylcarbamoyl-1-(methoxycarbonylmethyl)piperidine-4-carboxylate

HRID 862123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862123
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH:6]=1)=[O:4].Cl.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[K+].[K+]>CO.C1(C)C=CC=CC=1.[Pt]=O.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:7]([C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH2:6]1)=[O:4]

Komponenten

9

Edukt 4

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22097574Methyl 2-(dimethylcarbamoyl)pyridine-4-carboxylate

Produkt 1

HCID 22097566Methyl-2-dimethylcarbamoyl-1-(methoxycarbonylmethyl)piperidine-4-carboxylateAusbeute 96.296,297 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 82844Platinum oxide (PtO)KatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of compound 28 (55.4 g, 0.27 mmole), conc. HCl (16 ml) in MeOH (62 ml) was hydrogenated over platinum oxide (1 g) at 8 kg/cm2 for 24 hours. The catalyst was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting oil was used without further purification. A mixture of crude intermediate compound hydrochloride, methyl bromoacetate (61 g, 0.4 mole) and K2CO3 (73.5 g, 0.53 mole) in toluene (200 ml) was heated at 70° C. for 3 hours. After cooling the reaction mixture, H2O (200 ml) was added and extracted with EtOAc (200 ml×2). The combined organic extracts were dried over MgSO4 and concentrated down. The crude oil was purified by silica gel chromatography EtOAc as eluent to give 29 (69.8 g, 0.26 mole, 97%).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting oil was used without further purification
  4. additionwas added
  5. extractionextracted with EtOAc (200 ml×2)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated down
  8. customThe crude oil was purified by silica gel chromatography EtOAc as eluent

Quellen und Nachweise

ORD-Eintrag
ord-42f77fa11c424f6bb447d8ac93fe2d2c
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716965

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