Dimethylformamide → 2-benzyl-6-[(3R,4R)-3,4-difluoropyrrolidine-1-yl]-3-iodopyridine

HRID 1359343ノート

反応式

HRID 1359343 の反応式
[I:1]N1C(=O)CCC1=O.CN(C)C=O.[CH2:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]2[CH2:31][C@@H:30]([F:32])[C@H:29]([F:33])[CH2:28]2)[N:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:14]([C:21]1[C:26]([I:1])=[CH:25][CH:24]=[C:23]([N:27]2[CH2:28][C@@H:29]([F:33])[C@H:30]([F:32])[CH2:31]2)[N:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 697594382-Benzyl-6-[(3r,4r)-3,4-difluoropyrrolidine-1-yl]pyridine

生成物 1

HCID 697590462-benzyl-6-[(3R,4R)-3,4-difluoropyrrolidine-1-yl]-3-iodopyridine収率 100.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

94 mg of N-iodosuccinic acid imide was added little by little to 5.0 ml of an N,N-dimethylformamide solution containing 104 mg of 2-benzyl-6-[(3R,4R)-3,4-difluoropyrrolidine-1-yl]pyridine under ice-cooling, followed by stirring overnight as it was. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic phase was washed with an aqueous sodium thiosulfate solution, water and brine, and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (10:1), to give 152 mg of the target compound.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with an aqueous sodium thiosulfate solution, water and brine
  4. customthe solvent was removed
  5. washeluted with hexane/ethyl acetate (10:1)

出典と根拠

ORDレコード
ord-d1a8f7464bda4a56a5fdd641b333ee2a
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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