Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180055, compound

HRID 601838Notes

Reaction equation

HRID 601838 reaction equation
O=[C:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=2[CH2:4][CH2:3]1.[F:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[C:19]([F:21])[CH:20]=1>>[F:14][C:15]1[CH:16]=[C:17]([CH:2]2[C:9]3[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=3[CH2:4][CH2:3]2)[CH:18]=[C:19]([F:21])[CH:20]=1.[F:14][C:15]1[CH:16]=[C:17]([C:2]2[C:9]3[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=3[CH2:4][CH:3]=2)[CH:18]=[C:19]([F:21])[CH:20]=1

Participants

4

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178505930HCID 178505930, compound

Product 2

HCID 59180055HCID 59180055, compoundHCID 66874402HCID 66874402, compound

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.5 g, 2.79 mmol) was reacted with 3,5-difluorophenylmagnesium bromide (14 mL, 6.97 mmol, 0.5 M in THF, 2.5 equiv) according to General Procedure 3 to give methyl 4-(3,5-difluorophenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6 (with 5% Pd/C), and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane afforded the title compound: 85 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.27 (ddt, 1H), 2.73-3.00 (m, 3H), 3.84 (s, 3H), 4.17-4.23 (m, 1H), 6.60-6.67 (m, 2H), 6.69-6.75 (m, 2H), 9.01 (br. s, 1H) and 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −110.76 (t, J=8.00 Hz).

Sources & evidence

ORD record
ord-1e8bce941e764dd095267fd7e132c0db
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…