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

HRID 601843Notes

Reaction equation

HRID 601843 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[C:16]3[CH:15]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[NH:13][C:12]=3[CH2:11][CH:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1>[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:16]3[CH:15]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[NH:13][C:12]=3[CH2:11][CH2:10]2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 1

HCID 66874027Methyl 4-(3,5-dimethylphenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 59180128Methyl 4-(3,5-dimethylphenyl)-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 (0.5 g, 2.79 mmol) and 3,5-dimethylphenylmagnesium bromide (14 mL, 6.97 mmol, 0.5 M in THF, 2.5 equiv) were reacted according to General Procedure 3 to give the endo olefin-containing compound methyl 4-(3,5-dimethylphenyl)-1,6-dihydrocyclopenta[b]pyrrole-2-carboxylate, which was then hydrogenated according to General Procedure 6 (with 5% Pd/C), and was purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.20-2.36 (m, 7H), 2.71-2.98 (m, 3H), 3.83-3.86 (m, 3H), 4.17 (t, J=7.35 Hz, 1H), 6.49 (s, 1H), 6.67 (d, J=1.42 Hz, 1H), 6.82-6.88 (m, 2H), 9.02 (br. s, 1H).

Workup

  1. customwas purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-6cbc41ff3889477c8247fc601ae5958b
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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