Hydrochloric Acid → (R)-3-(5-hydroxyhexyl)-1,7-dimethylxanthine

HRID 1835697

반응식

HRID 1835697 반응식
C([O:4][C@H:5]([CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[N:17]=[CH:16][N:15]([CH3:19])[C:14]=2[C:13](=[O:20])[N:12]([CH3:21])[C:11]1=[O:22])(=O)C.Cl.C(OCC)C>CO>[OH:4][C@H:5]([CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[N:17]=[CH:16][N:15]([CH3:19])[C:14]=2[C:13](=[O:20])[N:12]([CH3:21])[C:11]1=[O:22]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 54338253(R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine

생성물 1

HCID 11637713(R)-3-(5-hydroxyhexyl)-1,7-dimethylxanthine수율 85%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirring solution of (R)-3-(5-acetoxyhexyl)-1,7-dimethylxanthine (0.28 g, 0.87 mmol) in methanol (20 ml) was added an anhydrous solution of hydrogen chloride in ethyl ether (1 M, 2.6 ml, 2.6 mmol). After refluxing for 4 hours, the mixture was concentrated under reduced pressure. The residue was treated with saturated aqueous solution of sodium bicarbonate solution (30 ml) and extracted with dichloromethane (3×20 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (30 ml), dried over sodium sulfate and concentrated under reduced pressure to give (R)-3-(5-hydroxyhexyl)-1,7-dimethylxanthine (0.20 g, 85% yield) as a colorless oil that solidified on standing.

후처리

  1. temperatureAfter refluxing for 4 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was treated with saturated aqueous solution of sodium bicarbonate solution (30 ml)
  4. extractionextracted with dichloromethane (3×20 ml)
  5. washThe combined extracts were washed with saturated aqueous sodium chloride solution (30 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-05a4f91104be4353a2d1edd52020da99
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774130B2

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