Propane sultone → 3-(cyclopropylamino)propane-1-sulfonic Acid

HRID 2175239ノート

反応式

HRID 2175239 の反応式
[CH2:1]1[CH2:7][S:4](=[O:6])(=[O:5])[O:3][CH2:2]1.[CH:8]1([NH2:11])[CH2:10][CH2:9]1>C1COCC1>[CH:8]1([NH:11][CH2:2][CH2:1][CH2:7][S:4]([OH:3])(=[O:6])=[O:5])[CH2:10][CH2:9]1

参加物

4

反応物 2

HCID 14264Propane sultoneHCID 69828Cyclopropylamine

生成物 1

HCID 114011103-(cyclopropylamino)propane-1-sulfonic Acid収率 17%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a solution of 1,3-propane sultone (2.246 g, 18.39 mmol) in THF (20.0 mL) was added cyclopropanamine (1.214 mL, 17.51 mmol) at room temperature. Upon completion of addition, the reaction mixture was stirred at 40° C. for 30 min, at which point the mixture became a thick white paste. At the conclusion of this period, the reaction mixture was vigorously stirred at 65° C. for 2 h. After cooling to room temperature, the resulting solid was collected by filtration to afford the tilted compound (0.522 g, 17% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.67 (br. s, 1H), 3.12 (t, J=6.9 Hz, 2H), 2.72-2.63 (m, 1H), 2.60 (t, J=6.8 Hz, 2H), 2.51-2.46 (m, 1H), 1.97-1.85 (m, 2H), 0.79-0.70 (m, 4H).

後処理

  1. additionUpon completion of addition
  2. stirringAt the conclusion of this period, the reaction mixture was vigorously stirred at 65° C. for 2 h
  3. temperatureAfter cooling to room temperature
  4. filtrationthe resulting solid was collected by filtration

出典と根拠

ORDレコード
ord-c9aa8f09952e421f9572d2bf07c16cb6
出典データセット
uspto-grants-2015_06
特許番号
US09062028B2

反応ノート

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