Aluminium lithium hydride → 3-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine

HRID 2084613

反応式

HRID 2084613 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18](=O)[NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 227338424-(4-Fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one

生成物 1

HCID 46913-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of lithium aluminium hydride in tetrahydrofuran (1.0M solution, 2 ml, 2.0 mmol) was added over ten minutes to a well stirred solution of 4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one (0.41 g, 0.96 mmol) in tetrahydrofuran (7 ml), maintaining the temperature below 25° C. The reaction solution was stirred for 2 hours and then quenched first of all with water (0.16 ml), then with 15% aqueous sodium hydroxide solution (0.1 ml), and finally with water again (0.4 ml). The reaction mixture was stirred for 0.5 hours to complete the precipitation, diluted with dichloromethane (30 ml) and filtered. The filtrate was evaporated in vacuo to give the title product with a trans/cis ratio=72:28. Yield 90%.

後処理

  1. temperaturemaintaining the temperature below 25° C
  2. customquenched first of all with water (0.16 ml)
  3. stirringThe reaction mixture was stirred for 0.5 hours
  4. customthe precipitation
  5. additiondiluted with dichloromethane (30 ml)
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

出典と根拠

ORDレコード
ord-fb0e71c853f743018e8c5ddad34674a8
出典データセット
uspto-grants-2004_04
特許番号
US06716985B2

関連ノート

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