Reaktion #43459

Reaktionsgleichung

1,1-Dimethylethyl (3S)-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate

HCl

1,4-dioxane

→

desired product

Ausbeute 100.0%

Phenylmethyl [(3R)-3-piperidinylmethyl]carbamate

Ausbeute 100.0%

Lösungsmittel

DCM

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas consumed
2. 2
   EinengenThe reaction was concentrated in vacuo
3. 3
   Sonstigeto give a thick gum
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   SonstigeThe aqueous phase was separated
6. 6
   workup.ADDITIONtreated with solid Na2CO3
7. 7
   ExtraktionThe product was then extracted into CHCl3 (3×)
8. 8
   Trocknenthe combined organic phases were dried (Na2SO4)
9. 9
   Einengenconcentrated

Vorschrift

1,1-Dimethylethyl (3S)-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (˜9.3 mmol) was dissolved in DCM (25 mL) and treated with a 4M HCl solution in 1,4-dioxane (24 mL, 96 mmol). The reaction was stirred at room temperature for 3 h, at which time LC/MS indicated that all starting material was consumed. The reaction was concentrated in vacuo to give a thick gum. This material was dissolved in water and extracted with ethyl acetate. The aqueous phase was separated and treated with solid Na2CO3 to bring the pH to ˜10. The product was then extracted into CHCl3 (3×) and the combined organic phases were dried (Na2SO4) and concentrated to yield the desired product as an orange oil (2.3 g, 100% for two steps).

Quelle