TBAF tetrahydrofuran → 2-Hydroxymethyl-6-(3-dipropylaminopropyl)naphthalene

HRID 1173991Notes

Reaction equation

HRID 1173991 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH:14]=[CH:13]2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>>[OH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH:16]=2)[CH:11]=1

Participants

3

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 23079316[3-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propyl]dipropylamine

Product 1

HCID 230791542-Hydroxymethyl-6-(3-dipropylaminopropyl)naphthaleneYield 50.9%

Procedure

The compound (1.28 g) obtained in Example 121-8 was added with a 1 mol/l TBAF/THF solution (6.20 ml) and stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off. Then, the residue was dissolved in chloroform and added with distilled water, followed by stirring. The solution was extracted with chloroform and the extract was then washed with saturated saline solution. The resulting organic layer was dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (472 mg) as a brown liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThen, the residue was dissolved in chloroform
  4. additionadded with distilled water
  5. stirringby stirring
  6. extractionThe solution was extracted with chloroform
  7. washthe extract was then washed with saturated saline solution
  8. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  9. distillationSubsequently, the solvent was distilled off
  10. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-eaf2344b60b547788dc115888bafa8c3
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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