Methyl iodide → Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate

HRID 1399978ノート

反応式

HRID 1399978 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1.[Li+].[CH3:24]C([N-]C(C)C)C.CI>C1COCC1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]1[CH2:13][CH2:14][C:15]([CH3:24])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17]1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 4082309Ethyl 4-(1,3-dioxoisoindolin-2-yl)cyclohexanecarboxylate

生成物 1

HCID 58074352Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of ii (0.30 g, 1.0 mmol) in THF (10 mL) was cooled to −78° C. followed by dropwise addition of LDA (1.60 M in THF, 1.88 mL, 3.0 mmol) at −78° C. The mixture was stirred at −78° C. for 30 min followed by addition of methyl iodide (0.311 mL, 5.0 mmol) at −78° C. The temperature of the reaction mass was slowly raised up to RT and left to stir overnight. The reaction was cooled to 0° C. and quenched by dropwise addition of saturated NH4Cl solution (30 mL). The reaction was extracted with EtOAc (3×50 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to obtain iii (0.30 g, 97%). MS 316.12 [M+H]+.

後処理

  1. temperatureThe temperature of the reaction mass was slowly raised up to RT
  2. waitleft
  3. stirringto stir overnight
  4. temperatureThe reaction was cooled to 0° C.
  5. customquenched by dropwise addition of saturated NH4Cl solution (30 mL)
  6. extractionThe reaction was extracted with EtOAc (3×50 mL)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5f588f845ce54fd38c1e7945e9b7cc3c
出典データセット
uspto-grants-2014_12
特許番号
US08906902B2

反応ノート

読み込み中…