3-(Piperidine-1-sulfonyl)benzoic acid → (3-(Piperidin-1-ylsulfonyl)phenyl)methanol

HRID 1967557ノート

反応式

HRID 1967557 の反応式
[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13](O)=[O:14])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C1COCC1.O>[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH2:13][OH:14])[CH:16]=[CH:17][CH:18]=2)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

5

反応物 2

HCID 7678893-(Piperidine-1-sulfonyl)benzoic acidHCID 4311764Sodium borohydride

生成物 1

HCID 65750537(3-(Piperidin-1-ylsulfonyl)phenyl)methanol収率 105.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-(Piperidin-1-ylsulfonyl)benzoic acid (7.00 g) was dissolved in THF (70 mL), and at 0° C., N,N′-carbodiimidazole (6.32 g) was added thereto and stirred at 0° C. for 4 hours. A solution prepared by dissolving sodium borohydride (1.97 g) in water (10 mL) was dropwise added to the reaction liquid, and then stirred at 0° C. for 1 hour. Water was added thereto, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient) to give the entitled compound (7.01 g, 100%) as a colorless oil.

後処理

  1. customA solution prepared
  2. additionwas dropwise added to the reaction liquid
  3. stirringstirred at 0° C. for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried with sodium sulfate
  7. customThe drying agent was removed through filtration
  8. customthe solvent was evaporated off under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 100%, gradient)

出典と根拠

ORDレコード
ord-7f37e1f358a04d139700ae9a0b0c8d92
出典データセット
uspto-grants-2013_04
特許番号
US08420823B2

反応ノート

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