(S)-1-Benzyl-3-ethylpiperazine-2,5-dione → (3S)-1-Benzyl-3-ethylpiperazine

To a solution of the product of example 69 part a) (5.68 g) in THF (30 ml) at 0° C. was added LAH (100 ml, 1.0M in THF) dropwise. The resulting solution was heated at reflux overnight. The reaction mixture was cooled to RT and quenched by cautious sequential addition of water (3.8 ml), 15% aq NaOH (3.8 ml), and water (11.4 ml). The precipitous solution was diluted with EtOAc and filtered through Celite. The residue was washed with EtOAc (3×100 ml) and the combined organics concentrated in vacuo. The crude product was dissolved in DCM, filtered through Celite and the solvent removed in vacuo to give the sub-titled product as a yellow oil (4.74 g).

1. temperatureThe resulting solution was heated
2. temperatureat reflux overnight
3. customquenched by cautious sequential addition of water (3.8 ml), 15% aq NaOH (3.8 ml), and water (11.4 ml)
4. additionThe precipitous solution was diluted with EtOAc
5. filtrationfiltered through Celite
6. washThe residue was washed with EtOAc (3×100 ml)
7. concentrationthe combined organics concentrated in vacuo
8. dissolutionThe crude product was dissolved in DCM
9. filtrationfiltered through Celite
10. customthe solvent removed in vacuo

ORD record

ord-5235d51d11f04949a64de3f9996e89c6

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524715B2