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

HRID 1359292ノート

反応式

HRID 1359292 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9379879dfd004c228923b35531334951
出典データセット
uspto-grants-2003_07
特許番号
US06599917B1

反応ノート

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