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

HRID 733093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733093
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.O.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(N(CC)CC)C>O1CCCC1>[CH3:35][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 2 of Example 7) in tetrahydrofuran (150 mL) was stirred at room temperature for 10 min. To this suspension, a solution of p-toluensulfonic acid monohydrate (52.4 g, 276 mmol) in tetrahydrofuran (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 h. After cooling down to room temperature, triethylamine (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 triethylamine. The resulting white suspension was stirred at room temperature for 6 h and it was filtered and the obtained solid was washed with tetrahydrofuran (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 h
  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 tetrahydrofuran (100 mL×2)
  8. customdried at 50° C. for 5 h

Quellen und Nachweise

ORD-Eintrag
ord-99b97c2c25fa47a08f62c254c7786679
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589109B2

Notizen zur Reaktion

Wird geladen…