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Formaldehyde → 1-[4-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester

HRID 554024
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 554024
[CH3:1][C:2]12[CH2:22][CH:6]([N:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][CH2:18][C:19](O)=O)=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:24])([CH3:23])[CH2:3]2.[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27].C=O.O>C1(C)C=CC=CC=1>[CH3:30][O:29][C:25]([CH:26]1[CH2:19][CH2:18][N:17]([C:14]2[CH:13]=[CH:12][C:11]([C:9]([N:7]3[CH2:8][C:2]4([CH3:1])[CH2:22][CH:6]3[CH2:5][C:4]([CH3:23])([CH3:24])[CH2:3]4)=[O:10])=[CH:16][CH:15]=2)[CH2:27]1)=[O:28]
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Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 962WaterHCID 7294Methyl Acrylate2×HCID 67016360[4-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenylamino]-acetic acid

Produkt 1

HCID 249502821-[4-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-pyrrolidine-3-carboxylic acid methyl esterAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

[4-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenylamino]-acetic acid (1.3 g, 3.93 mmol), methyl acrylate (275 μl, 3.03 mmol) and paraformaldehyde (636 mg, 21.18 mmol) were dissolved in toluene (180 ml) in a three necked reaction flask equipped with a water separator. The mixture was stirred at reflux temp. for 3 hrs at which time a small portion of methyl acrylate (40 μl) was added. The resulting mixture was stirred at reflux temp. for an additional 16 hrs. and evaporated. The residue was dissolved in EtOAc (50 ml) and washed with water (2×25 ml), dried (Na2SO4), filtered and evaporated in vacuo. The resulting residue was purified by column chromatography (silica gel) using first pure heptane (300 ml) followed by a mixture of EtOAc-Heptane (1:1) as eluents. Pure fractions were collected and evaporated to dryness affording 603 mg (52%) of 1-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester as an oil.

Aufarbeitung

  1. temperatureat reflux temp
  2. stirringThe resulting mixture was stirred
  3. temperatureat reflux temp
  4. customand evaporated
  5. dissolutionThe residue was dissolved in EtOAc (50 ml)
  6. washwashed with water (2×25 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe resulting residue was purified by column chromatography (silica gel)
  11. additionfollowed by a mixture of EtOAc-Heptane (1:1) as eluents
  12. customPure fractions were collected
  13. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e1c7c782aaf14271a73080683548a889
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08048908B2

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