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

HRID 344742

Reaction equation

HRID 344742 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([NH2:7])=[O:6])[CH3:4].O=[C:9]([CH3:17])[CH2:10][CH2:11][C:12](OCC)=[O:13]>O>[CH3:4][C@@H:3]1[N:2]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2([CH3:17])[NH:7][C:5]1=[O:6]

Participants

4

Reactant 2

HCID 10883Ethyl levulinateHCID 2775816(S)-2-aminopropanamide hydrochloride

Product 1

HCID 10241189(3S)-3,7a-Dimethyl-2,5-dioxohexahydro-1H-pyrrolo[1,2-a]imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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° C. (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)+.

Sources & evidence

ORD record
ord-9ff0fd4018d34c3dbc8819294fbba072
Source dataset
uspto-grants-1991_10
Patent number
US05053422

Linked notes

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