Triethylamine → 1-{[4-(Aminomethyl)piperidin-1-yl)methyl]cyclobutanecarboxylic acid 4-methylbenzenesulfonate

HRID 645986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645986
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:21]([OH:23])=[O:22])[CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1)=O)(C)(C)C.[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1.O.CCN(CC)CC>C1COCC1>[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1.[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:21]([OH:23])=[O:22])[CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 672328231-[(4-{[(Tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]cyclobutanecarboxylic acid

Produkt 1

HCID 866021201-{[4-(Aminomethyl)piperidin-1-yl)methyl]cyclobutanecarboxylic acid 4-methylbenzenesulfonateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a 500 mL, 3-necked round bottom flask under N2, a mixture of 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]cyclobutane carboxylic acid (30 g, 92 mmol, Step 6) in THF (150 mL) was stirred at room temperature for 10 min. To this suspension, a solution of p-TsOH H2O (52.4 g, 276 mmol) in THF (150 mL) was added at room temperature. After stirring at that temp for 10 min, the resulting solution was heated under reflux condition for 3 hrs. After cooling down to room temperature, Et3N (28.1 mL, 202 mmol) was added very slowly during the period of 1 h with seeding. The white precipitate was formed during the addition of Et3N. The resulting white suspension was stirred at room temperature for 6 h and it was filtered and the obtained solid was washed with THF (100 mL×2), dried at 50° C. for 5 h to give 35 g (96%) of the titled compound as white powder

Aufarbeitung

  1. stirringAfter stirring at that temp for 10 min
  2. temperaturethe resulting solution was heated
  3. temperatureunder reflux condition for 3 hrs
  4. temperatureAfter cooling down to room temperature
  5. stirringThe resulting white suspension was stirred at room temperature for 6 h
  6. filtrationit was filtered
  7. washthe obtained solid was washed with THF (100 mL×2)
  8. customdried at 50° C. for 5 h

Quellen und Nachweise

ORD-Eintrag
ord-ddd5701c84b749219ab00c219fa313a3
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705020B2

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