L-Leucinol → 3,6-Diisobutylhexahydropyrazine-2,5-dione

HRID 926975Notes

Reaction equation

HRID 926975 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:3][OH:4]>[Ru].O1CCOCC1>[CH2:5]([CH:2]1[NH:1][C:3](=[O:4])[CH:2]([CH2:5][CH:6]([CH3:8])[CH3:7])[NH:1][C:3]1=[O:4])[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 111307L-Leucinol

Product 1

HCID 1370063,6-Diisobutylhexahydropyrazine-2,5-dione

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Refluxing a dioxane solution of (S)-2-amino-4-methylpentan-1-ol with complex 1 (1 mol %) led to 64% isolated yield of the cyclic dipeptide, 3,6-diisobutylpiperazine-2,5-dione 7b after workup (Table 9, entry 1). The product structure was confirmed by MS, NMR spectroscopies.

Sources & evidence

ORD record
ord-f69790c66fed489d94215120793426c2
Source dataset
uspto-grants-2016_03
Patent number
US09290441B2

Reaction notes

Loading…