Reaktion #798184

Reaktionsgleichung

citric acid

(2S,5R)-5-(benzyloxyamino)piperidine-2-carboxylic acid, dihydrochloride

Potassium carbonate

N-(trimethylsilylethyloxycarbonyloxy)succinimide

sodium hydroxide

→

title compound

Ausbeute 86.4%

(2S,5R)-5-((Benzyloxy)amino)-1-(2-trimethylsilylethoxycarbonyl)piperidine-2-carboxylic acid

Ausbeute 86.4%

Lösungsmittel

water

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas elevated to room temperature
2. 2
   workup.STIRRINGby stirring overnight
3. 3
   Extraktionmonohydrate, and extracted with ethyl acetate (50 mL) twice
4. 4
   WaschenThe organic layer was washed with water and saturated brine
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

To (2S,5R)-5-(benzyloxyamino)piperidine-2-carboxylic acid, dihydrochloride (3.23 g, 10 mmol) described in Example 11 were added 1,4-dioxane (10 mL), water (15 mL) and 5M sodium hydroxide (6 mL), and stirred under ice cooling. Potassium carbonate (1.38 g), N-(trimethylsilylethyloxycarbonyloxy)succinimide (2.85 g) were added further to the mixture, and the temperature was elevated to room temperature, followed by stirring overnight. The mixture was adjusted to pH 4 with citric acid.monohydrate, and extracted with ethyl acetate (50 mL) twice. The organic layer was washed with water and saturated brine and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane=1:1→1:0) to afford 3.41 g of the title compound (yield 86%).

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