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

HRID 601812Notes

Reaction equation

HRID 601812 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.[F:14][C:15]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:16]=1[CH2:17][Mg]Cl>[Pd]>[F:14][C:15]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:16]=1[CH2:17][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

4

Reactant 2

HCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178505761HCID 178505761, compound

Product 1

HCID 59180239Methyl 4-(2,4-difluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

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 2,4-difluorobenzylmagnesium chloride (0.25 M in diethyl ether, 28 mL, 7 mmol) according to General Procedure 3. The resulting exo-olefin ((E)-methyl 4-(2,4-difluorobenzylidene)-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 0-20% EtOAc/heptane to afford the title compound: 0.062 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.05-2.15 (m, 1H), 2.55-2.65 (m, 1H), 2.65-2.75 (m, 2H), 2.79 (d, J=7.4, 2H), 3.25-3.35 (m, 1H), 3.81 (s, 3H), 6.38 (d, J=1.4 Hz, 1H), 6.78-6.90 (m, 2H), 7.10-7.15 (m, 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 0-20% EtOAc/heptane

Sources & evidence

ORD record
ord-53bdd46b5440496abfca42de64bb969b
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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