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

HRID 16592
ノート
印刷プレビュー

反応式

HRID 16592 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 521998p-Toluenesulfonic acid monohydrateHCID 685851131-[(4-{[(Tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]cyclopentanecarboxylic acid

生成物 1

HCID 866021181-{[4-(Aminomethyl)piperidin-1-yl]methyl}cyclopentanecarboxylic acid 4-methylbenzenesulfonate収率 97.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
70 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-31b021853ff84fc5bb229651be2e6c57
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737163B2

反応ノート

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