Water → 2-Hydroxymethyl-6-(4-dipropylaminobutyl)naphthalene

HRID 1174003Notes

Reaction equation

HRID 1174003 reaction equation
C([Si](O[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH2:20][CH:21]=[CH:22]OC)[CH:15]=2)[CH:10]=1)(C)C)(C)(C)C.[OH2:25].[CH2:26]([NH:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28].[C:33]([BH3-])#N.[Na+]>C1COCC1.CO.C(O)(=O)C>[OH:25][CH2:33][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:29]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:27][CH3:28])[CH:15]=2)[CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8902DipropylamineHCID 5003444Sodium cyanoborohydrideHCID 66941419t-Butyl-[6-(4-methoxy-3-butenyl)-naphthalen-2-yloxy]-dimethyl-silane

Product 1

HCID 210843912-Hydroxymethyl-6-(4-dipropylaminobutyl)naphthalene

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The compound (263 mg) obtained in Example 124-1 was dissolved in THF (2.0 ml) and then added with distilled water (2.0 ml) and acetic acid (2.0 ml), followed by stirring overnight at room temperature. After completion of the reaction, the solvent was distilled off and the residue was obtained. Dipropylamine (253 mg) was dissolved in anhydrous methanol (5.0 ml). Then sodium cyanoborohydride (69.5 mg), acetic acid (3.0 ml), and the residue described above dissolved in anhydrous methanol were added to the solution, followed by stirring at room temperature for 3 days under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and added with a saturated aqueous sodium bicarbonate solution, followed by stirring. Then, the solution was subjected to extraction with chloroform. The extract was washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (70.0 mg) as a yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was obtained
  4. additionwere added to the solution
  5. stirringby stirring at room temperature for 3 days under a nitrogen atmosphere
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off
  8. dissolutionThe residue was dissolved in chloroform
  9. additionadded with a saturated aqueous sodium bicarbonate solution
  10. stirringby stirring
  11. extractionThen, the solution was subjected to extraction with chloroform
  12. washThe extract was washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  13. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  14. distillationThe solvent was distilled off
  15. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-24f55ef5f5eb48b2a36294ff7e3eabe2
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…