Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → Methyl 4-(3-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601821Notes

Reaction equation

HRID 601821 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.[Br:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][Mg]Br>>[Br:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][CH: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.[Br:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)/[CH:18]=[C:2]1\[CH2:3][CH2:4][C:5]2[NH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:9]\1=2

Participants

4

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178419662HCID 178419662, compound

Product 2

HCID 59180244Methyl 4-(3-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 66873522(E)-methyl 4-(3-bromobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Procedure

The title compound was synthesized in two steps. Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (1.50 g, 8.37 mmol) was reacted with 3-bromobenzylmagnesium bromide (84 mL, 21 mmol) according to General Procedure 3 to give (E)-methyl 4-(3-bromobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6, and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-30% EtOAc/heptane to afford the title compound: 1.034 g. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.03-2.11 (m, 1H), 2.47-2.56 (m, 1H), 2.59-2.73 (m, 2H), 2.78 (d, 7.47 Hz, 2H), 3.24-3.32 (m, 1H), 3.72 (s, 3H), 6.32 (d, 1.76 Hz, 1H), 7.20-7.28 (m, 3H), 7.37-7.40 (m, 1H), 7.43 (br s, 1H).

Sources & evidence

ORD record
ord-87bb67a762e7497d986a80fa408d772b
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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