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

HRID 2167176Notes

Reaction equation

HRID 2167176 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:3][OH:4]>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

3

Reactant 1

HCID 111307L-Leucinol

Product 1

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

Reagents, catalysts & solvents 1

HCID 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 31, entry 1). The product structure was confirmed by MS, NMR spectroscopies.

Sources & evidence

ORD record
ord-092e7c836dd1440698cf310709a61f2e
Source dataset
uspto-grants-2015_06
Patent number
US09045381B2

Reaction notes

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