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

HRID 1919856ノート

反応式

HRID 1919856 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>C1COCC1>[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

3

反応物 1

HCID 7678893-(Piperidine-1-sulfonyl)benzoic acid

生成物 1

HCID 65750537(3-(Piperidin-1-ylsulfonyl)phenyl)methanol収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-(piperidin-1-ylsulfonyl)benzoic acid (538 mg, 2.00 mmol) in dry THF (8 mL) under nitrogen was added a solution of borane-THF complex in dry THF (1.0 M, 8 mL, 8.00 mmol) and the mixture then stirred for 18 hours at room temperature. The reaction was then quenched by the addition of excess methanol and evaporated in vacuo. The residue was partitioned between ethyl acetate and 2N HCl, and the separated organic layer washed successively with water and saturated brine, before being dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was purified using automated flash column chromatography on silica gel (gradient of 0 to 60% ethyl acetate in petrol) to afford (3-(piperidin-1-ylsulfonyl)phenyl)methanol (320 mg, 1.25 mmol, 63%).

後処理

  1. customThe reaction was then quenched by the addition of excess methanol
  2. customevaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 2N HCl
  4. washthe separated organic layer washed successively with water and saturated brine
  5. dry with materialbefore being dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified

出典と根拠

ORDレコード
ord-5e71e2327d6b4abe8e41cfd13c0cf3ac
出典データセット
uspto-grants-2012_05
特許番号
US08168673B2

反応ノート

読み込み中…