2-Fluoropyridine → (cis)-3-Hydroxy-4-(pyridin-2-ylaminomethyl)-piperidine-1-carboxylic acid benzyl ester

HRID 1351499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351499
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH2:18])[C@H:13]([OH:19])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C@H:13]([OH:19])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 97462-FluoropyridineHCID 58635348(cis)-4-Aminomethyl-3-hydroxy-piperidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 69415336(cis)-3-Hydroxy-4-(pyridin-2-ylaminomethyl)-piperidine-1-carboxylic acid benzyl ester

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of (cis)-4-aminomethyl-3-hydroxy-piperidine-1-carboxylic acid benzyl ester (0.1 g, 378 mmol) and 2-fluoropyridine (0.25 mL) was heated to 120° C. for 24 h. The reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent evaporated to give a (cis)-3-hydroxy-4-(pyridin-2-ylaminomethyl)-piperidine-1-carboxylic acid benzyl ester crude product, which was purified by flash column chromatography (50% EtOAc hexane to 5% MeOH EtOAc). M.S (M+1): 342

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4610db330df441abaa2952c50d0498b4
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217716B2

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