Sulfuric Acid → (2R)-4-(3-pyridyl)-1,2-butanediol

HRID 1935716ノート

反応式

HRID 1935716 の反応式
C([O:8][CH2:9][C@H:10]([OH:19])[CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)C1C=CC=CC=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>[Pd].CO>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][CH2:11][C@@H:10]([OH:19])[CH2:9][OH:8])[CH:14]=1

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 15457204(2R)-1-O-benzyl-4-(3-pyridyl)-1,2-butandiol

生成物 1

HCID 12972952(2R)-4-(3-pyridyl)-1,2-butanediol収率 63%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

Under argon gas, MeOH (70 mL) was added to 10% palladium-on-carbon (1.0 g). Then, the (2R)-1-O-benzyl-4-(3-pyridyl)-1,2-butanediol produced in Example 3 (28.25 g, 100 mmol) and sulfuric acid (19.6 g, 200 mmol) were added. After degassing under reduced pressure, a hydrogen atmosphere was established. The pressure was increased to 3 atm. and the mixture was stirred at room temperature for 16 hours. The palladium-on-carbon was filtered off and the solvent was distilled off under reduced pressure, whereupon a light-yellow oil was obtained. To this oil was added a saturated aqueous solution of sodium hydrogencarbonate for neutralization, followed by concentration under reduced pressure. The residue was extracted with ethyl acetate twice (200 mL each). The organic layers were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the oily residue was purified by silica gel column chromatography (Merck's Kieselgel 60, MeOH/ethyl acetate=1/9) to give 10.52 g (isolation yield: 63%) of (2R)-4-(3-pyridyl)-1,2-butanediol (yellow oil).

後処理

  1. customAfter degassing under reduced pressure
  2. temperatureThe pressure was increased to 3 atm.
  3. filtrationThe palladium-on-carbon was filtered off
  4. distillationthe solvent was distilled off under reduced pressure, whereupon a light-yellow oil
  5. customwas obtained
  6. concentrationfollowed by concentration under reduced pressure
  7. extractionThe residue was extracted with ethyl acetate twice (200 mL each)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customthe oily residue was purified by silica gel column chromatography (Merck's Kieselgel 60, MeOH/ethyl acetate=1/9)

出典と根拠

ORDレコード
ord-11bb13d809914d079c468d5bdf467c10
出典データセット
uspto-grants-2002_05
特許番号
US06388086B1

反応ノート

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