Reaktion #1435747

Reaktionsgleichung

TFA

4-oxo-piperidine-1-carboxylic acid tert-butyl ester

morpholine

sodium cyanoborohydride

→

4-Piperidin-4-yl-morpholine

Lösungsmittel

ethanol

methylene chloride

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature over night
2. 2
   Sonstigethe reaction was quenched with addition of water (4 mL)
3. 3
   workup.STIRRINGThe mixture was stirred for 30 minutes
4. 4
   Filtrationthe white solid was filtered out
5. 5
   Sonstigethe filtrate was evaporated
6. 6
   SonstigeThe residue was partitioned between ether and water
7. 7
   Sonstigethe organic layer was separated
8. 8
   Trocknendried with sodium sulfate
9. 9
   SonstigeRemoval of solvent
10. 10
    Sonstigegave a white solid which
11. 11
    workup.STIRRINGThe solution was stirred at room temperature for 1 hour
12. 12
    Sonstigethe solvent was removed
13. 13
    Sonstigeto give a white solid

Vorschrift

To a stirred solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (Aldrich, 3.0 g, 15 mmol) in THF (25 mL), morpholine (Aldrich, 1.56 g, 18 mmol) and Ti(OiPr)4 (Aldrich, 5.58 mL) were added successively and the mixture was stirred at room temperature for 1 hour. Then, 15 mL of ethanol was added and followed by sodium cyanoborohydride (0.63 g, 10.05 mmol). The resulting mixture was stirred at room temperature over night and the reaction was quenched with addition of water (4 mL). The mixture was stirred for 30 minutes and the white solid was filtered out and the filtrate was evaporated. The residue was partitioned between ether and water and the organic layer was separated and dried with sodium sulfate. Removal of solvent gave a white solid which was treated with 40 mL of 50% TFA in methylene chloride. The solution was stirred at room temperature for 1 hour and the solvent was removed. The residue was lyophilized to give a white solid. 5.48 g, 98%. MS (m+H)+: 171.

Quelle