Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180218, compound

HRID 601847Notes

Reaction equation

HRID 601847 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.[CH2:14]([C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:14]([C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178419626HCID 178419626, compound

Product 2

HCID 59180218HCID 59180218, compoundHCID 66873702HCID 66873702, compound

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.64 g, 3.6 mmol) and (4-benzylphenyl)magnesium bromide were reacted according to General Procedure 3 to give methyl 4-(4-benzylphenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate. (4-Benzylphenyl)magnesium bromide was synthesized from 1-benzyl-4-bromobenzene. (In an inert Ar atmosphere, to a suspension of Mg (0.44 g, 18.2 mmol) turnings in 50 mL of THF was added very slowly (dropwise) 1-benzyl-4-bromobenzene, then catalytic amount of iodine was added. The reaction mixture was stirred for 30 min at room temperature, then 25 mL of THF was added and the mixture was stirred for 3 hours at 75-80° C. (gentle reflux of THF).) The methyl 4-(4-benzylphenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate was hydrogenated according to General Procedure 6 with 5% Pd/C and a hydrogen balloon, and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.23-2.35 (m, 1H), 2.71-2.97 (m, 3H), 3.82 (s, 3H), 3.96 (s, 2H), 4.20 (t, J=7.32 Hz, 1H), 6.63 (d, J=1.76 Hz, 1H), 7.09-7.15 (m, 5H), 7.16-7.23 (m, 2H), 7.28-7.32 (m, 2H), 8.84 (br. s, 1H).

Sources & evidence

ORD record
ord-a3d24c05e9494386b0b9f52598a8764e
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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