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

HRID 1691663ノート

反応式

HRID 1691663 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
75 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-aa926dd74e5040be9334fe8760707384
出典データセット
uspto-grants-2012_04
特許番号
US08153658B2

反応ノート

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