Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate → HCID 59180131, compound

HRID 601822Notes

Reaction equation

HRID 601822 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][CH:24]=1)[CH2:19][Mg]Br.ClC1C=C(C=CC=1Cl)/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][CH:24]=1)[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 67269526(E)-methyl 4-(3,4-dichlorobenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178490219HCID 178490219, compound

Product 1

HCID 59180131HCID 59180131, 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 (447 mg, 2.5 mmol) was reacted with 3-methoxybenzylmagnesium bromide (0.25 M in hexanes, (25 mL, 6.3 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(3-methoxybenzylidene)-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 chromatography, eluting with heptane-EtOAc, gradient 0 to 40% EtOAc to afford the title compound. 155 mg. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.04-2.21 (m, 1H) 2.50-2.63 (m, 1H) 2.62-2.71 (m, 2H) 2.72-2.86 (m, 2H) 3.23-3.36 (m, 1H) 3.81 (s, 6H) 6.44 (d, J=1.56 Hz, 1H) 6.72-6.85 (m, 3H) 7.22 (t, J=7.78 Hz, 1H) 8.76 (br. s, 1H).

Workup

  1. customThe title compound was synthesized in two steps
  2. customThe crude product was purified by chromatography
  3. washeluting with heptane-EtOAc, gradient 0 to 40% EtOAc

Sources & evidence

ORD record
ord-1819fd2e44a14f4c9a348059eaf56581
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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