1-(3-Cyclopentyl-propyl)-3-(4-nitro-phenyl)-1,3-dihydro-imidazol-2-one → 1-(4-Amino-phenyl)-3-(3-cyclopentyl-propyl)-imidazolidin-2-one
Reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH:13]=[CH:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)[C:10]2=[O:23])[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(OCC)(=O)C>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([N:11]2[CH2:12][CH2:13][N:9]([CH2:8][CH2:7][CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:10]2=[O:23])=[CH:19][CH:18]=1Participants
Procedure
A mixture of the product from Example 49 (3.7 g, 11.7 mmol) and 10% palladium on activated carbon (0.74 g) in ethyl acetate (200 mL) was placed under an atmosphere of hydrogen overnight. The mixture was filtered through a pad of Celite with excess ethyl acetate, and the filtrate was concentrated to a crude brown oil. The crude was purified by silica gel chromatography (gradient elution from 2:1 hexanes/ethyl acetate to 1:1 hexanes/ethyl acetate) to afford a pale orange solid (2.01 g, 60%). Mp 97-99° C.; Rf =0.1 (2:1 hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 7.20 (d, 2 H), 6.72 (d, 1 H), 6.63 (d, 1 H), 6.57 (d, 2 H), 5.09 (br s, 1 H), 3.50 (t, 2 H), 1.72 (m, 3 H), 1.59 (m, 6 H), 1.26 (m, 2 H), 1.03 (m, 2 H); MS (FAB) m/z 286 (MH+).
Workup
- filtrationThe mixture was filtered through a pad of Celite with excess ethyl acetate
- concentrationthe filtrate was concentrated to a crude brown oil
- customThe crude was purified by silica gel chromatography (gradient elution from 2:1 hexanes/ethyl acetate to 1:1 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-359ac626401c4f3ca8cc085e35aeae59
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06051586
Reaction notes
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