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Cesium carbonate → (R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester

HRID 77332
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HRID 77332 반응식
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22](OS(C)(=O)=O)[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Li+]>CN(C)C=O.O>[CH2:1]([O:3][C:4]([CH:5]1[C@H:22]2[CH2:21][CH:20]([CH2:26][CH2:25][CH2:24][CH2:23]2)[N:6]1[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])=[O:32])[CH3:2]
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 66321Lithium iodideHCID 86653279HCID 86653279, 화합물

생성물 1

HCID 67155158(R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester수율 77%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
80 °C

실험 절차

To a solution of (R)—N-naphthalene-2-sulfonyl (3-methanesulfonyloxy-cycloheptyl)glycine ethyl ester (0.60 g, 1.24 mmol) in N,N-dimethylformamide (5 mL) is added cesium carbonate (1.21 g, 3.71 mmol) followed by lithium iodide (0.249 g, 1.86 mmol), and the reaction is heated to 80° C. for 3 hours. The reaction is cooled to ambient temperature, diluted with water, and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product is purified by column chromatography (20% hexanes-ethyl acetate) to afford the title compound as a white solid (0.37 g, 77% yield). LCMS (m/z): 388.10 (M+1).

후처리

  1. temperatureThe reaction is cooled to ambient temperature
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography (20% hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-436a20a90b49487ea90e45c889fa580f
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841291B2

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