Methyl iodide → 2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

HRID 1359292노트

반응식

HRID 1359292 반응식
[H-].[Na+].[CH2:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:20][C@@H:19]([OH:21])[C@H:18]([OH:22])[CH2:17]2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23]I>O1CCCC1>[CH2:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:17][C@@H:18]([O:22][CH3:23])[C@H:19]([OH:21])[CH2:20]2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 693610072-Benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]pyridine

생성물 1

HCID 111968722-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

800 mg of oily (60%) sodium hydride was added little by little to a mixture of 5.35 g of 2-benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidine-1-yl]pyridine and 40 ml of tetrahydrofuran while stirring, followed by stirring as it was for one hour. Then 1.24 ml of methyl iodide was added thereto, followed by stirring as it was overnight. The mixture was extracted with ethyl acetate-water, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 30% ethyl acetate/hexane, to give 2.18 g of the target compound.

후처리

  1. stirringby stirring as it
  2. stirringby stirring as it
  3. waitwas overnight
  4. extractionThe mixture was extracted with ethyl acetate-water
  5. washthe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. washeluted with 30% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-9379879dfd004c228923b35531334951
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599917B1

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