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Methanol → 3-methyl-5-[3-(2-pyrrolidin-1-yl-ethylamino)-propyl]-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

HRID 2191450
Notes
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Reaction equation

HRID 2191450 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:26])=[C:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13]OS(C)(=O)=O)=[O:5])[CH3:2].C(OCC)(=O)C.CO.[N:35]1([CH2:40][CH2:41][NH2:42])[CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:26])=[C:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][NH:42][CH2:41][CH2:40][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 887MethanolHCID 13441-PyrrolidineethanamineHCID 8857Ethyl AcetateHCID 592500502-(tert-butyl) 4-ethyl 3-methyl-5-(3-((methylsulfonyl)oxy)propyl)-1H-pyrrole-2,4-dicarboxylate

Product 1

HCID 592500823-methyl-5-[3-(2-pyrrolidin-1-yl-ethylamino)-propyl]-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl esterYield 63.5%

Procedure

5-(3-Methanesulfonyloxy-propyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1 g (8.462 g, 21.75 mmol) was dissolved in 2-pyrrolidin-1-yl-ethylamine (6.3 ml, 49.79) under stirring, the resulting solution was stirred at room temperature overnight. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was added with ethyl acetate (200 ml) and a little methanol until a clear solution was obtained. The mixture was washed with water (30 ml×3), saturated brine (40 ml×2) and concentrated under reduced pressure to obtain light brown oil. The oil was purified by silica gel column chromatography to obtain the title compound 3-methyl-5-[3-(2-pyrrolidin-1-yl-ethylamino)-propyl]-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 28a (4.488 g, yield 63.5%) as a yellow oil.

Workup

  1. stirringthe resulting solution was stirred at room temperature overnight
  2. washThe mixture was washed with water (30 ml×3), saturated brine (40 ml×2)
  3. concentrationconcentrated under reduced pressure
  4. customto obtain light brown oil
  5. customThe oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-36492c1154b84159866147d06ab36f3a
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329682B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes