Triethylamine → 4-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylic acid 4-methylbenzenesulfonate

HRID 16585

Reaktionsgleichung

C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1)=O)(C)(C)C.[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:31][CH:32]=1.O.CCN(CC)CC>CC(O)C>[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:31][CH:32]=1.[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

In a 300 mL, 3-necked round bottom flask under N2, 4-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylic acid (10 g, 28 mmol, Step 11) was placed and a solution of p-TsOH H2O (16 g, 84 mmol) in IPA (150 mL) was poured at room temperature. The resulting mixture was stirred at 60° C. for 7 h under N2 and Et3N (8.6 mL, 62 mmol) was added dropwise slowly during the period of 2 hr with seeding. The white precipitate was formed during the addition of Et3N. The resulting white suspension was stirred at 60° C. for 3 h, at 50° C. for 5 h and at room temperature for 10 h. The suspension was filtered and the obtained solid was washed with IPA (100 mL), dried at 50° C. for 5 h to give 10.5 g (87%) of the titled compound as white powder.

Aufarbeitung

stirringThe resulting white suspension was stirred at 60° C. for 3 h, at 50° C. for 5 h and at room temperature for 10 h
filtrationThe suspension was filtered
washthe obtained solid was washed with IPA (100 mL)
customdried at 50° C. for 5 h

Quellen und Nachweise

ORD-Eintrag: ord-a7eb81d30f2d4529aa24f726b141655c
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737163B2

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