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

HRID 733098

反応式

HRID 733098 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: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.O.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(N(CC)CC)C>C(O)(C)C>[CH3:37][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

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 521998p-Toluenesulfonic acid monohydrateHCID 672319944-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylic acid

生成物 1

HCID 866021174-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylic acid 4-methylbenzenesulfonate収率 87.5%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
60 °C

実験手順

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 4 of Example 8) was placed and a solution of p-toluenesulfonic acid monohydrate (16 g, 84 mmol) in i-propanol (150 mL) was poured at room temperature. The resulting mixture was stirred at 60° C. for 7 h under N2 and triethylamine (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 triethylamine. 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 i-propanol (100 mL), dried at 50° C. for 5 h to give 10.5 g (87%) of the titled compound as white powder.

後処理

  1. 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
  2. filtrationThe suspension was filtered
  3. washthe obtained solid was washed with i-propanol (100 mL)
  4. customdried at 50° C. for 5 h

出典と根拠

ORDレコード
ord-7499e16d2e324b48bbd7bbfa2857bc2b
出典データセット
uspto-grants-2009_09
特許番号
US07589109B2

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