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

HRID 654115Notes

Reaction equation

Cl.[NH2:2][CH:3]([C:5]([NH2:7])=[O:6])[CH3:4].O=[C:9]([CH3:17])[CH2:10][CH2:11][C:12](OCC)=[O:13]>>[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

Reactant 2

HCID 10883Ethyl levulinate

HCID 123172862-Aminopropanamide hydrochloride

Product 1

HCID 57150387(3R,S)-3,7a-Dimethyl-2,5-dioxohexahydro-1 H-pyrrolo[1,2-a]imidazole

Procedure

DL-Alaninamide hydrochloride (6.9 g), 0.055 mol) and ethyl 4-oxopentanoate (6.7 g, 0.043 mol) were reacted together according to the procedure of Example 2 to give the title compound, 1.65 g (22.8%), m.p 184°-192°. NMR (DMSO-d6 : deltaH =8.80 (bs, 1H, NH); 3.90 (q, J=7.5 Hz, 1H, CHCH3) 3.00-2.00 (c.a., 4H, CH2CH2); 1.42 (s, 3H, C--CH3); 1.22 (d, J=7.5 Hz, 1H, CHCH3)

Sources & evidence

ORD record: ord-19cd80425ef343948389895dcae7b20e
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130319

Reaction notes

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