[2-(4-Fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone → [2-(4-Fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol

HRID 1243899Notes

Reaction equation

HRID 1243899 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:43]=[CH:42][C:11]([CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[C:14]=2[C:25]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:29][CH:28]=2)=[O:26])=[CH:10][CH:9]=1>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[C:14]=2[CH:25]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:29][CH:28]=2)[OH:26])=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 10481006[2-(4-Fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 10413616[2-(4-Fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add LAH solution (2 mL, 1M/THF) to a stirred solution of [2-(4-fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (380 mg) in THF (5 mL) at room temperature. Heat the mixture to reflux for 1 h, cool to r.t. and quench with aq. NaHCO3. Dilute the mixture with CH2Cl2 and wash with water and brine, dry over MgSO4, filter and concentrate to afford [2-(4-fluoro-benzyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol. Use the product without further purification.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux for 1 h
  3. customquench with aq. NaHCO3
  4. additionDilute the mixture with CH2Cl2
  5. washwash with water and brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-4d3d3b34f16b47f898ae7d13fa490c7f
Source dataset
uspto-grants-2006_10
Patent number
US07119206B2

Reaction notes

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