Boron tribromide → [6-Hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

HRID 2223680Notes

Reaction equation

HRID 2223680 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)=[O:18])=[C:12]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41]C)[CH:11]=[CH:10]2>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)=[CH:23][CH:24]=1)=[O:18])=[C:12]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[OH:41])[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 22046618[6-Methoxy-2-(2-methoxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 9982673[6-Hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanoneYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add BBr3 (0.3 mL) dropwise to a stirred solution of [6-methoxy-2-(2-methoxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (650 mg, 1.28 mmol) in CH2Cl2 (15 mL) at room temperature. Stir for 1 h and add an additional aliquot of BBr3 (0.2 mL). Continue stirring for 1 h and quench with MeOH and 2-methyl-2-butene. Load the resulting solution on an SCX cartridge, wash with MeOH and elute with 2M NH3/MeOH. Purify the resulting product by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2) to afford [6-hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (161 mg, 26%).

Workup

  1. stirringContinue stirring for 1 h
  2. customquench with MeOH and 2-methyl-2-butene
  3. washLoad the resulting solution on an SCX cartridge, wash with MeOH
  4. washelute with 2M NH3/MeOH
  5. customPurify the resulting product by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-283df53bc0a843029a685d001a4959ed
Source dataset
uspto-grants-2008_05
Patent number
US07375229B2

Reaction notes

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