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

HRID 1675086노트

반응식

HRID 1675086 반응식
[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

참가 물질

5

반응물 2

HCID 21480587Benzyl 4-hydroxy-4-(pyridin-3-yl)piperidine-1-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-dae26efd5249466eb1c34c55007141d4
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003649B2

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