HCID 10345296, compound → HCID 10480612, compound

HRID 1243894Notes

Reaction equation

HRID 1243894 reaction equation
[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=2[C:9]=1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:23][CH:22]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=2[C:9]=1[CH:19]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:25][CH:26]=1)[OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10345296HCID 10345296, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10480612HCID 10480612, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve crude (2-benzyl-6-methoxy-benzo[b]thiophen-3-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone in THF (10 mL) at r.t. Add LAH solution (3 mL of 1M/THF) dropwise while stirring. Continue stirring for 20 min. and quench with aq. NaHCO3. Dilute the reaction mixture with CH2Cl2 and wash with water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0–5% (2M NH3 in MeOH)/CH2Cl2) to yield (2-benzyl-6-methoxy-benzo[b]thiophen-3-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol (755 mg, 84%, 2 steps).

Workup

  1. customquench with aq. NaHCO3
  2. additionDilute the reaction mixture with CH2Cl2
  3. washwash with water and brine
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude product by flash chromatography (0–5% (2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-75737e434c174ce3bcf656485d2fab05
Source dataset
uspto-grants-2006_10
Patent number
US07119206B2

Reaction notes

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