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Imidazole → tert-butyl 9-(2-(1H-imidazol-1-yl)ethoxy)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1253723
ノート
印刷プレビュー

反応式

HRID 1253723 の反応式
CS(O[CH2:6][CH2:7][O:8][CH:9]1[CH2:26][CH2:25][C:12]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:11][CH2:10]1)(=O)=O.[H-].[Na+].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>CN(C=O)C.C(OCC)(=O)C>[N:29]1([CH2:6][CH2:7][O:8][CH:9]2[CH2:10][CH2:11][C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:25][CH2:26]2)[CH:33]=[CH:32][N:31]=[CH:30]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

6

反応物 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 86645837tert-Butyl 9-(2-(methylsulfonyloxy)ethoxy)-3-azaspiro[5.5]undecane-3-carboxylate

生成物 1

HCID 66700676tert-butyl 9-(2-(1H-imidazol-1-yl)ethoxy)-3-azaspiro[5.5]undecane-3-carboxylate収率 84%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
25 °C

実験手順

A solution of tert-butyl 9-(2-(methylsulfonyloxy)ethoxy)-3-azaspiro[5.5]undecane-3-carboxylate (2.68 mmol, 1.0 eq.) in DMF (10 ml) was added dropwise to a stirred mixture of NaH (8.04 mmol, 3.0 eq.) and imidazole (5.36 mmol, 2.0 eq.) in DMF (15 ml) at 0° C. and the resulting mixture was stirred at 25° C. for 16 h. The reaction mixture was diluted with ethyl acetate (300 ml) and washed with water (200 ml) and brine (200 ml). The organic layer was dried over sodium sulfate and concentrated under reduce pressure to give the crude product which was purified by silica gel column chromatography eluting with 2% MeOH in MC to afford the desired product as a yellow oil. Yield: 84%

後処理

  1. washwashed with water (200 ml) and brine (200 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customto give the crude product which
  5. customwas purified by silica gel column chromatography
  6. washeluting with 2% MeOH in MC

出典と根拠

ORDレコード
ord-cf4f6cfb47c2470d88b9223cbfef24ad
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08455475B2

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