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

HRID 736417

Reaction equation

C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1)=O)(C)(C)C.[CH3:25][C:26]1[CH:27]=[CH:28][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:30][CH:31]=1.O.CCN(CC)CC>C1COCC1>[CH3:25][C:26]1[CH:27]=[CH:28][C:29]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:30][CH:31]=1.[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 70 °C

Procedure

In a 100 mL, 2-necked round bottom flask, to a mixture of 1-[(4-{[(tert-butoxycarbonyl) amino]methyl}piperidin-1-yl)methyl]cyclopentanecarboxylic acid (5 g, 14.7 mmol, Step 7) in THF (25 mL), a solution of p-TsOH H2O (8.4 g, 44 mmol) in THF (25 mL) was added at room temperature. The resulting mixture was stirred at 70° C. for 3 h under N2 and it was cooled down to room temperature. To this solution, Et3N (6 mL, 44 mmol) was added dropwise slowly. The white precipitate was formed during the addition of Et3N and the resulting mixture was stirred at room temperature for 14 h. The suspension was filtered and the obtained solid was washed with THF (10 mL), dried at 50° C. for 5 h to give 5.9 g (97%) of the titled compound as a white solid.

Workup

temperatureit was cooled down to room temperature
stirringthe resulting mixture was stirred at room temperature for 14 h
filtrationThe suspension was filtered
washthe obtained solid was washed with THF (10 mL)
customdried at 50° C. for 5 h

Sources & evidence

ORD record: ord-e86f5d45bff94887b2b1a0c2f70abc63
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595329B2

Linked notes

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