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

HRID 2354563노트

반응식

HRID 2354563 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21226445Aluminium lithium hydride용매

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-6f0cb2e9a35c4679ab5f51723e69fac4
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754719B2

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