3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one → (+)-3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine

HRID 2354563ノート

反応式

HRID 2354563 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:12]3=O)=[CH:9][C:4]=2[O:3][CH2:2]1>C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

参加物

4

反応物 1

HCID 684532313-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one

生成物 1

HCID 68451530(+)-3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21226445Aluminium lithium hydride溶媒

実験手順

To a solution of (−)-3-benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one (1.73 g, 5.3 mmol) in THF (21 ml), LiAlH4 (6.5 ml of a 1 M solution in THF, 6.5 mmol) is added dropwise at rt. The mixture is refluxed for 2.5 h, cooled to rt, quenched with water and filtered over Celite®. The filtrate is evaporated, the residue dissolved in AcOEt, washed with water and brine, and the aq. layers are reextracted with AcOEt, the combined organic layers are dried over Na2SO4 and evaporated to give (+)-3-benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine ([α]Drt=28.2° (c=0.5, EtOH)).

後処理

  1. temperatureThe mixture is refluxed for 2.5 h
  2. customquenched with water
  3. filtrationfiltered over Celite®
  4. customThe filtrate is evaporated
  5. dissolutionthe residue dissolved in AcOEt
  6. washwashed with water and brine
  7. dry with materialthe combined organic layers are dried over Na2SO4
  8. customevaporated

出典と根拠

ORDレコード
ord-6f0cb2e9a35c4679ab5f51723e69fac4
出典データセット
uspto-grants-2010_07
特許番号
US07754719B2

反応ノート

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