Hydrochloric Acid → Pilocarpine

HRID 1461496

반응식

HRID 1461496 반응식
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

참가 물질

8

반응물 5

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

생성물 1

HCID 5910Pilocarpine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-6a06e6c1fa664926b4924ce17f1cf3e1
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075452

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