Benzyl 4-hydroxy-4-(pyridin-3-yl)piperidine-1-carboxylate → 4-(Pyridin-3-yl)piperidin-4-ol

HRID 1675086

反応式

HRID 1675086 の反応式
[OH:1][C:2]1([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:7][CH2:6][N:5](C(OCC2C=CC=CC=2)=O)[CH2:4][CH2:3]1.[H][H]>C(O)C.[Pd]>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:2]2([OH:1])[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]2)[CH:19]=1

参加物

5

反応物 2

HCID 21480587Benzyl 4-hydroxy-4-(pyridin-3-yl)piperidine-1-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 49891674-(Pyridin-3-yl)piperidin-4-ol収率 80%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Benzyl 4-hydroxy-4-(pyridin-3-yl)piperidine-1-carboxylate (32.7 g, 104.69 mmol) was dissolved in ethanol (350 mL) and hydrogenated over 10% palladium on carbon (3.2 g) at 2 bar pressure at 30° C. After hydrogen uptake was complete, the mixture was filtered through a pad of diatomaceous earth to remove the catalyst and the pad was washed with ethanol. The filtrate was concentrated to dryness under vacuum to give an oil which crystallised on standing overnight. The solid was triturated with MTBE (100 mL), collected by filtration, washed with MTBE (2×50 ml) and dried in a vacuum oven at 40° C. to afford 4-(pyridin-3-yl)piperidin-4-ol (14.9 g, 80%) as a solid.

後処理

  1. filtrationthe mixture was filtered through a pad of diatomaceous earth
  2. customto remove the catalyst
  3. washthe pad was washed with ethanol
  4. concentrationThe filtrate was concentrated to dryness under vacuum
  5. customto give an oil which
  6. customcrystallised
  7. customThe solid was triturated with MTBE (100 mL)
  8. filtrationcollected by filtration
  9. washwashed with MTBE (2×50 ml)
  10. customdried in a vacuum oven at 40° C.

出典と根拠

ORDレコード
ord-dae26efd5249466eb1c34c55007141d4
出典データセット
uspto-grants-2011_08
特許番号
US08003649B2

関連ノート

読み込み中…