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Water → N-Methyl-N-{2-[(tributylstannyl)methoxy]ethyl}cyclohexaneamine

HRID 642962
ノート
印刷プレビュー

反応式

HRID 642962 の反応式
[H-].[Na+].[CH:3]1([N:9]([CH3:13])[CH2:10][CH2:11][OH:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:14]([Sn:18]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19]I)[CH2:15][CH2:16][CH3:17].O>O1CCCC1.C(OCC)(=O)C>[CH3:13][N:9]([CH2:10][CH2:11][O:12][CH2:19][Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2775822-(Cyclohexylmethylamino)ethanolHCID 10862926Tributyl(iodomethyl)stannane

生成物 1

HCID 59259719N-Methyl-N-{2-[(tributylstannyl)methoxy]ethyl}cyclohexaneamine収率 86%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a mixture of sodium hydride (50%, 241 mg, 5.0 mmol) and tetrahydrofuran (20 ml) was added 2-[cyclohexyl(methyl)amino]ethanol (791 mg, 5.0 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 60° C. for 30 minutes. After the reaction mixture was cooled at 0° C. (external temperature), to the reaction mixture was added dropwise a solution of tributyl-iodomethyl-tin (2.2 g, 5.0 mmol) in tetrahydrofuran (5 ml), and the reaction mixture was stirred at 60° C. for 1 hour. After the reaction mixture was cooled at room temperature (external temperature), water was added to stop the reaction. Ethyl acetate was added to the reaction mixture, and the organic layer was separated. After the organic layer was washed with water, an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (790.7 mg, 4.3 mmol, 85%).

後処理

  1. temperatureAfter the reaction mixture was cooled at 0° C. (external temperature)
  2. stirringthe reaction mixture was stirred at 60° C. for 1 hour
  3. additionwas added
  4. customthe reaction
  5. customthe organic layer was separated
  6. washAfter the organic layer was washed with water
  7. distillationan aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel)

出典と根拠

ORDレコード
ord-210dbaacbcd64b4dbdd1bdd888419e6a
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07696347B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート