methyl 4-(3-tert-butoxy-3-oxoprop-1-enyl)-1H-pyrrole-2-carboxylate → methyl 4-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate

HRID 601895Notes

Reaction equation

HRID 601895 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH:7]=[CH:8][C:9]1[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[NH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[NH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66874596methyl 4-(3-tert-butoxy-3-oxoprop-1-enyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 59180142methyl 4-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylateYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-(3-tert-butoxy-3-oxoprop-1-enyl)-1H-pyrrole-2-carboxylate (2.0 g, 7.96 mmol) in EtOAc (20 mL) under nitrogen was added 10% Pd/C. The flask was evacuated and refilled with hydrogen three times. The reaction mixture was stirred for 2 h. The catalyst was removed by filtration through Celite and the filtrate was concentrated to give methyl 4-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate as a white solid (2.02 g, 100%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.43 (s, 9H), 2.48 (t, J=7.59 Hz, 2H), 2.77 (t, J=7.54 Hz, 2H), 3.84 (s, 3H), 6.77 (dd, J=2.37, 1.93 Hz, 2H), 930 (br s, 1H); LCMS-MS (ESI+) 198.2 (M-isobutylene).

Workup

  1. customThe flask was evacuated
  2. additionrefilled with hydrogen three times
  3. customThe catalyst was removed by filtration through Celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dbf7eb177f1d49ad83bb44ae8c851ebb
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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