Dipropylamine → [3-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propyl]dipropylamine

HRID 1173990Notes

Reaction equation

HRID 1173990 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].C([BH3-])#N.[Na+].C(OC)(OC)OC.[Si:19]([O:26][CH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH:34]=[C:33]([CH2:38][CH2:39][CH:40]=O)[CH:32]=[CH:31]2)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CO>[Si:19]([O:26][CH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[CH:34]=[C:33]([CH2:38][CH2:39][CH2:40][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])[CH:32]=[CH:31]2)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 8902DipropylamineHCID 9005Trimethyl orthoformateHCID 5003444Sodium cyanoborohydrideHCID 230791943-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehyde

Product 1

HCID 23079316[3-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propyl]dipropylamineYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dipropylamine (363 mg) was dissolved in anhydrous methanol (20 ml) and then added with sodium cyanoborohydride (281 mg), trimethyl orthoformate (0.490 ml), and the compound (981 mg) obtained in Example 121-7, followed by stirring overnight at room temperature under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off. Then, the residue was dissolved in chloroform and added with a saturated aqueous sodium bicarbonate solution, followed by stirring. The solution was extracted with chloroform and the extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. After that, the 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 (1.28 g) 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 a saturated aqueous sodium bicarbonate solution
  5. stirringby stirring
  6. extractionThe solution was extracted with chloroform
  7. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  8. dry with materialAfter that, the 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-0915bf9cf86a43aaa6f9e1f4ea5c0592
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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