Aluminium lithium hydride → [1-Benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanol

HRID 270043ノート

反応式

HRID 270043 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])([C:14](OCC)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:14][OH:15])([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 59833634Ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylate

生成物 1

HCID 68961767[1-Benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanol収率 61.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A stirred solution of ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylate (1.85 g, 5.2 mmol) in diethyl ether was cooled on ice/sodium chloride. Lithium aluminium hydride (5.8 mL, 1.0 M in diethyl ether) was added drop wise. After stirring at room temperature for 2 hrs the mixture was re-cooled on ice, quenched with water/sodium hydroxide (10%) and stirred at room temperature for 1 hrs. The solids were filtered off, and the organic layer was dried over disodium sulphate, filtrated and concentrated. The crude material was purified on silica (dichloromethane/ethanol) to give 1.0 g (61%) the subtitle compound.

後処理

  1. temperaturewas re-cooled on ice
  2. customquenched with water/sodium hydroxide (10%)
  3. stirringstirred at room temperature for 1 hrs
  4. filtrationThe solids were filtered off
  5. dry with materialthe organic layer was dried over disodium sulphate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe crude material was purified on silica (dichloromethane/ethanol)

出典と根拠

ORDレコード
ord-18c3dc96c2444d1c8907860676f650a2
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

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