Ethyl 1-Benzyl-4-(3-methylphenylamino)-piperidine-4-carboxylate → 1-Benzyl-4-hydroxymethyl-4-(3-methylphenylamino)piperidine

HRID 565605ノート

反応式

HRID 565605 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)([C:20](OCC)=[O:21])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)C>[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([CH2:20][OH:21])([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 21193210Ethyl 1-Benzyl-4-(3-methylphenylamino)-piperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 211933021-Benzyl-4-hydroxymethyl-4-(3-methylphenylamino)piperidine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

To a slurry of lithium aluminum hydride (330 mg, 8.7 mmol) in anhydrous diethyl ether (25 mL) at 0° C., a solution of ethyl 1-benzyl-4-(3-methylphenylamino)piperidine-4-carboxylate (2.8 g, 7.94 mmol) in diethyl ether (10 mL) was added dropwise with the temp. of the reacting mixture maintained below 10° C. The resulting mixture was stirred at 0° C. for 30 min, and quenched with successive addition of water (0.33 mL), 15% aqueous NaOH (0.33 mL), and water (1 mL). The resultant slurry was stirred at room temp. for 30 min., and was filtered through a small plug of Celite. The filtrate was washed brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title alcohol as white solid.

後処理

  1. temperatureof the reacting mixture maintained below 10° C
  2. customquenched with successive addition of water (0.33 mL), 15% aqueous NaOH (0.33 mL), and water (1 mL)
  3. stirringThe resultant slurry was stirred at room temp. for 30 min.
  4. filtrationwas filtered through a small plug of Celite
  5. washThe filtrate was washed brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-0720541192894dbbb989f967ac88bd02
出典データセット
uspto-grants-2001_01
特許番号
US06172076B2

反応ノート

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