Tetrahydrofuran → Rel-[(3r,4s)-4-phenylpiperidin-3-yl]methanol

HRID 1691663노트

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HRID 1691663 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.O=[C:13]1[NH:18][CH2:17][C@H:16]([C:19](OC)=[O:20])[C@@H:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:14]1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[C:23]1([C@H:15]2[CH2:14][CH2:13][NH:18][CH2:17][C@@H:16]2[CH2:19][OH:20])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59178494methyl rel-(3R,4S)-6-oxo-4-phenylpiperidine-3-carboxylate

생성물 1

HCID 59977995Rel-[(3r,4s)-4-phenylpiperidin-3-yl]methanol수율 84.6%

시약·촉매·용매 2

HCID 962Water용매2회HCID 1140Toluene용매

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온도
75 °C

실험 절차

To a suspension of 1.8 g of lithium aluminum hydride in 40 mL of toluene—40 mL of THF was added 6.3 g of methyl rel-(3R,4S)-6-oxo-4-phenylpiperidine-3-carboxylate at room temperature. The reaction mixture was stirred at 75° C. for 35 hours. After completion of the reaction, it was cooled to room temperature, and 1.0 mL of water, 1.0 mL of a 1 M aqueous sodium hydroxide solution, and 1.0 mL of water added thereto in this order, followed by stirring for 10 minutes. This mixture was dried over anhydrous sodium sulfate, the insolubles were removed by filtration, and the filtrate was then concentrated under reduced pressure to obtain a white solid of 4.37 g of rel-[(3R,4S)-4-phenylpiperidin-3-yl]methanol as a crude product. ESI+: 192

후처리

  1. customAfter completion of the reaction, it
  2. temperaturewas cooled to room temperature
  3. stirringby stirring for 10 minutes
  4. dry with materialThis mixture was dried over anhydrous sodium sulfate
  5. customthe insolubles were removed by filtration
  6. concentrationthe filtrate was then concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aa926dd74e5040be9334fe8760707384
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153658B2

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