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

HRID 645979
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인쇄 미리보기

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HRID 645979 반응식
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
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참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 521998p-Toluenesulfonic acid monohydrateHCID 685851131-[(4-{[(Tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]cyclopentanecarboxylic acid

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5665953de3e141658bb55d8681534c8e
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07705020B2

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