Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180109, compound

HRID 601837Notes

Reaction equation

HRID 601837 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]=[CH:19][C:20]=1[F:21]>>[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]=[CH:19][C:20]=1[F:21].[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]=[CH:19][C:20]=1[F:21]

Participants

4

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178505835HCID 178505835, compound

Product 2

HCID 59180109HCID 59180109, compoundHCID 66873427HCID 66873427, 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 3,4-difluorophenylmagnesium bromide (14 mL, 7.0 mmol, 0.5 M in THF) according to General Procedure 3 to give methyl 4-(3,4-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 0-30% EtOAc/heptane affording the title compound. 0.333 g. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.16-2.27 (m, 1H), 2.70-2.98 (m, 3H), 3.75 (s, 3H), 4.22 (t, J=7.22 Hz, 1H), 6.53 (d, J=1.85 Hz, 1H), 7.02-7.07 (m, 1H), 7.11 (ddd, J=11.96, 7.86, 2.15 Hz, 1H), 7.21 (dt, J=10.68, 8.43 Hz, 1H), 10.68 (br. s, 1H).

Sources & evidence

ORD record
ord-003a25cae7aa4d7cada02766d1e6dbf6
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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