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

HRID 733093ノート

反応式

HRID 733093 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: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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-99b97c2c25fa47a08f62c254c7786679
出典データセット
uspto-grants-2009_09
特許番号
US07589109B2

反応ノート

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