Hydrochloric Acid → Pilocarpine

HRID 1461496

反応式

HRID 1461496 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][CH2:14][C@H:15]1[C:19](=[O:20])[O:18][CH2:17][C@@H:16]1[CH2:21][C:22]1[N:26]([CH3:27])[CH:25]=[N:24][CH:23]=1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.Cl>CCCCCC.O1CCCC1>[CH3:13][CH2:14][C@@H:15]1[C:19](=[O:20])[O:18][CH2:17][C@@H:16]1[CH2:21][C:22]1[N:26]([CH3:27])[CH:25]=[N:24][CH:23]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 91468(+)-IsopilocarpineHCID 178418339Butyllithium

生成物 1

HCID 5910Pilocarpine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

0.97 ml of a 15% solution of n-butyllithium in hexane is added at 0° C. to a solution of 0.21 ml of diisopropylamine in tetrahydrofuran. After stirring for 15 minutes and cooling to -78° C., 100 mg of (+)-isopilocarpine dissolved in 1 ml of tetrahydrofuran are added, and the mixture is stirred at -78° C. for 10 hours. After the addition of 1 g of 2,6-di-tert.-butyl-4-methylphenol, warming to room temperature and addition of 15 ml of hydrochloric acid (0.5 N), the layers are separated. The aqueous layer is washed twice with 25 ml of chloroform. Concentration of the organic layer and preparative separation on an HPLC column gives optically pure (+)-pilocarpine which is converted into the pilocarpine nitrate, m.p. 174° C., αD =+81° (c=1.618, water) with nitric acid (65%) in ethanol. Reference1 : R. S. Compagnone, H. Rapoport, J. Org. Chem. 51, 1713-1719 (1986)

後処理

  1. additionare added
  2. stirringthe mixture is stirred at -78° C. for 10 hours
  3. temperaturewarming to room temperature
  4. customthe layers are separated
  5. washThe aqueous layer is washed twice with 25 ml of chloroform
  6. customConcentration of the organic layer and preparative separation on an HPLC column

出典と根拠

ORDレコード
ord-6a06e6c1fa664926b4924ce17f1cf3e1
出典データセット
uspto-grants-1991_12
特許番号
US05075452

関連ノート

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