5-Methoxytryptamine → N-[2-(5-methoxy-1H-indol-3-yl)ethyl]oxolane-2-carboxamide

HRID 899550

반응식

HRID 899550 반응식
[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[O:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[C:20](Cl)=[O:21].C(OCC)(=O)C>C1C=CC=CC=1.CCOCC.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6](=[CH:5][CH:4]=1)[NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][C:20]([CH:16]1[CH2:17][CH2:18][CH2:19][O:15]1)=[O:21]

참가 물질

7

반응물 3

HCID 18335-MethoxytryptamineHCID 8857Ethyl AcetateHCID 551254Tetrahydro-2-furancarbonyl chloride

생성물 1

HCID 2987724N-[2-(5-methoxy-1H-indol-3-yl)ethyl]oxolane-2-carboxamide

시약·촉매·용매 3

HCID 241Benzene용매2회HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

5-Methoxytryptamine (540 mg, 2.84 mmole) was suspended in benzene (5 ml). The mixture was cooled in an ice bath and a solution of tetrahydro-2-furoyl chloride (390 μl, 3.7 mmole) in benzene (5 ml) was slowly added. The reaction mixture was stirred at room temperature for 15 hours and was diluted with ether (25 ml). It was extracted with water (25 ml), NaHCO3 solution (2×25 ml) and saturated NaCl solution (25 ml) dried (MgSO4) and the solvent was removed in vacuo. Further purification was obtained by column chromatography on silica gel. The solvent was 50% ethyl acetate in CH2Cl2. Fractions of 10 ml were collected and the product was eluted in fractions 19-32. The product was obtained as an oil. The yield was 220 mg (˜30%).

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionIt was extracted with water (25 ml), NaHCO3 solution (2×25 ml) and saturated NaCl solution (25 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customFurther purification
  6. customwas obtained by column chromatography on silica gel
  7. customFractions of 10 ml were collected
  8. washthe product was eluted in fractions 19-32
  9. customThe product was obtained as an oil

출처 및 근거

ORD 기록
ord-fac6d70cd4cf4056a38786fec980a090
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07355054B2

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