Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180059, compound

HRID 601824Notes

Reaction equation

HRID 601824 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]=[CH:22][C:23]=1[CH3:24])[CH2:18][Mg]Cl.COC1C=C(C=CC=1OC)/C=C1\CCC2NC(C(OC)=O)=CC\1=2>[Pd]>[CH3:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[CH3:24])[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

Participants

5

Reactant 3

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 67269380HCID 67269380, compoundHCID 178425360HCID 178425360, compound

Product 1

HCID 59180059HCID 59180059, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.50 g, 2.8 mmol) was reacted with 3,4-dimethyl-benzylmagnesium chloride (0.25 M in THF, 28.0 mL, 7.0 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(3,4-dimethylbenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) was then converted to the title compound by hydrogenation according to General Procedure 6 (with 5% Pd/C). The crude product was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-50% EtOAc/heptane to afford the title compound. 0.050 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.02-2.19 (m, 1H) 2.19-2.35 (m, 6H) 2.44-2.62 (m, 1H) 2.62-2.87 (m, 4H) 3.19-3.38 (m, 1H) 3.82 (s, 3H) 6.46 (d, J=1.56 Hz, 1H) 6.95 (d, J=7.52 Hz, 1H) 7.00 (s, 1H) 7.07 (d, J=7.42 Hz, 1H) 8.93 (br. s, 1H).

Workup

  1. customThe title compound was synthesized in two steps
  2. customThe crude product was purified by column chromatography (Isco CombiFlash)
  3. washeluting with a gradient of 0-50% EtOAc/heptane

Sources & evidence

ORD record
ord-073b969310f2499880d72b2466b7e798
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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