(S)-3-tert-Butyl-2,5-piperazinedione → (2S)-2-tert-Butylpiperazine

Temperatur

65 °C

Lithium aluminum hydride(1 M solution in THF, 40 mL, 40.0 mmol) was added drop wise to solution of (S)-2-tert-butylpiperazin-3,6-dione (1.5 g, 8.82 mmol) in THF (50 mL) at 0° C. The reaction mixture was stirred at room temperature for 7 days and at 65° C. for 17 h, then cooled to 0° C. and quenched sequentially with H2O (1.7 mL), 10% NaOH (2.2 mL) and H2O (3.4 mL). Ether (100 mL) was added to the reaction mixture, and stirring was continued for 1.5 h. The solid was filtered, the filtrate was concentrated and purified by column chromatography (silica gel, 33% EtOAc in hexanes) to afford (S)-2-tert-butylpiperazine (0.64 g, 52%) as a clear oil. 1H NMR and MS consistent.

1. temperaturecooled to 0° C.
2. customquenched sequentially with H2O (1.7 mL), 10% NaOH (2.2 mL) and H2O (3.4 mL)
3. additionEther (100 mL) was added to the reaction mixture
4. stirringstirring
5. waitwas continued for 1.5 h
6. filtrationThe solid was filtered
7. concentrationthe filtrate was concentrated
8. custompurified by column chromatography (silica gel, 33% EtOAc in hexanes)

ORD-Eintrag

ord-1f44ca578bd04d309896d32a4cb8b391

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07863271B2