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

HRID 601905Notes

Reaction equation

HRID 601905 reaction equation
O=[C:2]1[C:6]2[NH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:5]=2[CH2:4][CH2:3]1.[F:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[CH:19][CH:20]=1>[Pd]>[F:14][C:15]1[CH:20]=[C:19]([CH:2]2[C:6]3[NH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:5]=3[CH2:4][CH2:3]2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 59180137Methyl 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178505773HCID 178505773, compound

Product 1

HCID 59180190Methyl 6-(3-fluorophenyl)-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 6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (447 mg, 2.5 mmol) was reacted with (3-fluorophenyl)magnesium bromide (0.5 M in hexanes, 13 mL, 6.3 mmol) according to General Procedure 3. The resulting crude product was 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. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.24-2.35 (m, 1H), 2.61-2.71 (m, 1H), 2.71-2.81 (m, 1H), 2.87-2.98 (m, 1H), 3.81 (s, 3H), 4.24 (t, J=7.54 Hz, 1H), 6.71 (d, J=1.51 Hz, 1H), 6.81 (dt, J=9.81, 1.85 Hz, 1H), 6.88-6.93 (m, 2H), 7.25 (s, 1H), 8.60 (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-10f4a52d4cca45579742c421b99ce44a
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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