Methyl (E)-5-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-1H-pyrrole-2-carboxylate → methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate

HRID 601792Notes

Reaction equation

HRID 601792 reaction equation
[C:1]([O:5][C:6](=[O:18])/[CH:7]=[CH:8]\[C:9]1[NH:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)/C=C/C1NC(C(OC)=O)=CC=1)(C)(C)C>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[NH:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 66873605Methyl (E)-5-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-1H-pyrrole-2-carboxylateHCID 66873748Methyl (Z)-5-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-1H-pyrrole-2-carboxylate

Product 1

HCID 66873239methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (z)-methyl 5-(3-tert-butoxy-3-oxoprop-1-enyl)-1H-pyrrole-2-carboxylate or (E)-methyl 5-(3-tert-butoxy-3-oxoprop-1-enyl)-1H-pyrrole-2-carboxylate (13.6 g, 54.1 mmol, 2 equal batches) in EtOAc (200 mL) under nitrogen was added 10% Pd/C. The flask was flushed with hydrogen three times before allowing the reaction to stir under hydrogen for about 18 h. The catalyst was filtered off using Celite and the filtrate was concentrated to give 27.4 g methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate as a white solid (100%) for each stereoisomer. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9H), 2.54-2.59 (m, 2H), 2.90 (t, J=6.83 Hz, 2H), 3.83 (s, 3H), 5.97 (dd, J=3.49, 2.86 Hz, 1H), 6.81 (dd, J=3.61, 2.59 Hz, 1H), 9.30 (br s, 1H); LCMS-MS (ESI+) 197.86 (M-isobutylene).

Workup

  1. customThe flask was flushed with hydrogen three times
  2. customthe reaction
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5aa934da671b4e32946a15d94cfa859a
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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