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

HRID 1253723
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인쇄 미리보기

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HRID 1253723 반응식
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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회
HCID 8857
Ethyl Acetate
용매

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온도
25 °C

실험 절차

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%

후처리

  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

출처 및 근거

ORD 기록
ord-cf4f6cfb47c2470d88b9223cbfef24ad
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08455475B2

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