Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180231, compound

HRID 601823Notes

Reaction equation

HRID 601823 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][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:19][Mg]Cl.COC1C=C(C=CC=1)/C=C1\CCC2NC(C(OC)=O)=CC\1=2>[Pd]>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:19][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 67268992HCID 67268992, compoundHCID 178490608HCID 178490608, compound

Product 1

HCID 59180231HCID 59180231, 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-dimethoxy-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-dimethoxybenzylidene)-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 2.06-2.18 (m, 1H) 2.50-2.68 (m, 3H) 2.68-2.81 (m, 2H) 3.20-3.35 (m, 1H) 3.74-3.94 (m, 9H) 6.36-6.46 (m, 1H) 6.69 (d, J=1.76 Hz, 1H) 6.74 (dd, J=8.10, 1.56 Hz, 1H) 6.82 (d, J=8.10 Hz, 1H) 8.80 (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-7c12c0d6f0344f2fa66c84ab65c42937
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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