Ethyl levulinate → (3S)-3,7a-Dimethyl-2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole

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Reaction Steps

L-Alaninamide hydrochloride (20.7 g, 0.166 mol) and ethyl 4-oxopentanoate (20 g, 0.13 mol) were reacted together according to the procedure of Example 2 to give the title compound, 4.5 g (19.1%), m.p. 228°-230° (with decomposition), [alpha]D =+50.7° (c=3, H2O). NMR (CDCl3): deltaH =7.95 (bs, 1H, NH); 4.30 (q, J=8 Hz, 1H, CHCH3); 3.00-2.10 (c.a., 4H, CH2CH2); 1.60 (s, 3H, C-CH3 ; 1.45 (d, J=8 Hz, 3H, CH3CH). MS (E.I., 70 eV, 1.5 mA) m/z=168 (M+), 153 (M-CH3)+, 125 (M-CHNO)+, 112 (M-C3H4O)+.

Provenance & Evidence