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

HRID 2354563Notes

Reaction equation

HRID 2354563 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226445Aluminium lithium hydrideSolvent

Procedure

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)).

Workup

  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

Sources & evidence

ORD record
ord-6f0cb2e9a35c4679ab5f51723e69fac4
Source dataset
uspto-grants-2010_07
Patent number
US07754719B2

Reaction notes

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