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

HRID 601825Notes

Reaction equation

HRID 601825 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.[CH3:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[CH2:18][Mg]Br>>[CH3:14][C:15]1[CH:23]=[C:22]([CH:21]=[C:17]([CH3:18])[CH:16]=1)[CH2:24][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.[CH3:14][C:15]1[CH:23]=[C:22]([CH:21]=[C:17]([CH3:18])[CH:16]=1)/[CH:24]=[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 178424986HCID 178424986, compound

Product 2

HCID 59180193Methyl 4-(3,5-dimethylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 66873460(E)-methyl 4-(3,5-dimethylbenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

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-dimethylbenzylmagnesium bromide (28 mL, 6.97 mmol, 0.25 M in THF, 2.5 equiv) according to General Procedure 3 to give (E)-methyl 4-(3,5-dimethylbenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, followed by hydrogenation according to General Procedure 6. The title compound was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.07-2.18 (m, 1H) 2.33 (s, 6H) 2.50-2.77 (m, 4H) 2.77-2.84 (m, 1H) 3.30 (quin, J=7.08 Hz, 1H) 3.83 (s, 3H) 6.46 (d, J=1.46 Hz, 1H) 6.85 (s, 2H) 6.88 (s, 1H) 9.00 (br. s, 1H).

Sources & evidence

ORD record
ord-1dd5095cefca45b48e3251d8a530e8f2
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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