Ethyl Acetate → Methyl 4-(3-(tetrahydrofuran-3-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601835Notes

Reaction equation

HRID 601835 reaction equation
O1C=CC=C1[C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)/[CH:9]=[C:10]1\[CH2:11][CH2:12][C:13]2[NH:14][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:17]\1=2.[C:25]([O:28][CH2:29][CH3:30])(=O)[CH3:26]>[Pd]>[O:28]1[CH2:29][CH2:30][CH:26]([C:6]2[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=2)[CH2:9][CH:10]2[C:17]3[CH:16]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[NH:14][C:13]=3[CH2:12][CH2:11]2)[CH2:25]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 66873323(E)-methyl 4-(3-(furan-2-yl)benzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 59180060Methyl 4-(3-(tetrahydrofuran-3-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(E)-Methyl 4-(3-(furan-2-yl)benzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.066 g, 0.207 mmol) was dissolved in ethyl acetate (5 mL). Then palladium on carbon (5%) was added and the reaction placed under a hydrogen atmosphere using a balloon, stirred at room temperature for 5 h, then filtered through celite. The filtrate was concentrated and purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-25% EtOAc/heptane affording the title compound. 0.028 g.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography (Isco CombiFlash)
  4. washeluting with a gradient of 0-25% EtOAc/heptane affording the title compound

Sources & evidence

ORD record
ord-4806c9e166f24da7b5097cc37753756d
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…