5-(2-tert-butoxycarbonyl-vinyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester → 5-(2-tert-butoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 397430Notes

Reaction equation

HRID 397430 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:12]=[CH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][C:10]=1[CH3:11])=[O:5])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[CH:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 697084895-(2-tert-butoxycarbonyl-vinyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 697094735-(2-tert-butoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(2-tert-butoxycarbonyl-vinyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.48 g) in ethyl acetate (60 mL) and ethanol (30 mL) was hydrogenated using 1% palladium on carbon at room temperature for overnight to give 2.49 g (100%) of 5-(2-tert-butoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.12 (br s, 1H, NH), 5.74 (d, J=2.3 Hz, 1H), 4.17 (q, J=7.1 Hz, 2H, OCH2), 2.71 (t, J=7.5 Hz, 2H, CH2), 2.47 (t, J=7.5 Hz, 2H, CH2), 2.18 (s, 3H, CH3), 1.36 (s, 9H, 3×CH3), 1.28 (t, J=7.1 Hz, 3H, OCH2CH3). MS 282 [M++1].

Workup

  1. customat room temperature
  2. customfor overnight

Sources & evidence

ORD record
ord-ee81e5c2cd014a43970d746ff25b3eee
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Reaction notes

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