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

HRID 348737
ノート
印刷プレビュー

反応式

HRID 348737 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0718d365aefe4eb38e5d790838d53d10
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176227B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート