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Acetic Acid → n-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

HRID 350840
ノート
印刷プレビュー

反応式

HRID 350840 の反応式
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl>[CH3:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:10]=2)=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 31521093-(4-Methoxy-phenoxy)-propylamineHCID 5049666Sodium triacetoxyborohydrideHCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

生成物 1

HCID 21949684n-3-(4-Methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

3-tert-Butyldimethylsilyloxybenzaldehyde (1.5 g, 6.34 mmol) was dissolved in 1,2-dichloroethane (10.0 mL). Subsequently, 3-(4-methoxyphenoxy)propylamine (1.5 g, 8.25 mmol) was added thereto, and the resultant mixture was stirred for 20 minutes. At room temperature, sodium triacetoxyborohydride (1.75 g, 8.25 mmol) and acetic acid (495 mg, 8.25 mmol) were added thereto, and the mixture was stirred overnight. A saturated aqueous sodium hydrogencarbonate solution was added thereto. The reaction mixture was extracted with chloroform, and the organic layer was washed with brine. The resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound was obtained (1.9 g, 78%).

後処理

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with brine
  3. dry with materialto drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound
  4. customwas obtained (1.9 g, 78%)

出典と根拠

ORDレコード
ord-1f5970dd638c4c0a941f58a35a661d4a
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07183295B2

反応ノート

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