Methyl iodide → (5-Cyclopropyl-4-methyl-isoxazol-3-yl)-carbamic acid phenyl ester

HRID 45158

反応式

HRID 45158 の反応式
[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[CH:14]=[C:13]([CH:15]3[CH2:17][CH2:16]3)[O:12][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[CH3:20]CC[CH2-].C(=O)=O.CC(C)=O.CI>C1COCC1>[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[C:14]([CH3:20])=[C:13]([CH:15]3[CH2:17][CH2:16]3)[O:12][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 61028n-Butyl lithiumHCID 18522661Acetone cardiceHCID 59394551(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester

生成物 1

HCID 59394495(5-Cyclopropyl-4-methyl-isoxazol-3-yl)-carbamic acid phenyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester (0.368 g, 1.51 mmol) is dissolved in THF (10 mL) and cooled to −78° C. and flushed with nitrogen. N-butyllithium (2.17 mL, 3.47 mmol) is then added. The mixture is stirred in the dry ice/acetone bath for 30 minutes. Methyl iodide (0.10 mL, 1.66 mmol) is added neat and the reaction is stirred for 2 hours at −78° C. The reaction is quenched (0° C.) with 20 mL of a saturated solution of ammonium chloride, diluted with ethyl acetate and the organic layer is removed, dried (sodium sulfate) and concentrated to an oil that is purified via FCC (0-40% ethyl acetate:heptanes) to give the title compound as an oil. MS (ESI) m/z 259.20 (M+1).

後処理

  1. customflushed with nitrogen
  2. customThe reaction is quenched (0° C.) with 20 mL of a saturated solution of ammonium chloride
  3. additiondiluted with ethyl acetate
  4. customthe organic layer is removed
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated to an oil that
  7. customis purified via FCC (0-40% ethyl acetate:heptanes)

出典と根拠

ORDレコード
ord-7f3f3842e56e4a07967d61e5674b95f7
出典データセット
uspto-grants-2013_09
特許番号
US08541432B2

関連ノート

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