[6-Hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone → 6-(2-Hydroxy-benzyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol

HRID 1830513Notes

Reaction equation

HRID 1830513 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:22][CH:21]=1)=[O:19])=[C:13]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[OH:42])[CH:12]=[CH:11]2>C1COCC1>[OH:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[CH2:35][C:13]1[C:14]([CH:18]([OH:19])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:22][CH:21]=2)=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:7])[CH:17]=[CH:16]2

Participants

4

Reactant 2

HCID 9982673[6-Hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 100509856-(2-Hydroxy-benzyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-olYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add LAH solution (0.3 mL, 1M/THF) to a solution of [6-hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (150 mg, 0.31 mmol) in THF (3 mL) at r.t. Stir for 30 min and quench with aq. NaHCO3. Dilute with CH2Cl2, 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 afford 6-(2-hydroxy-benzyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol (123 mg, 82%).

Workup

  1. customquench with aq. NaHCO3
  2. additionDilute 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-89abcd28db0a4927804de3b3e6ce51b6
Source dataset
uspto-grants-2006_06
Patent number
US07067510B2

Reaction notes

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