Isopropyl iodide → Tert-butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate

HRID 643523ノート

反応式

HRID 643523 の反応式
[Li+].[CH3:2][CH:3]([N-]C(C)C)[CH3:4].[CH3:9][O:10][C:11]1([O:23][CH3:24])[CH2:15][CH2:14][CH:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]1.IC(C)C>C1COCC1.CCOCC>[CH:3]([C:13]1([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15][C:11]([O:23][CH3:24])([O:10][CH3:9])[CH2:12]1)([CH3:4])[CH3:2]

参加物

6

反応物 3

HCID 6362Isopropyl iodideHCID 2724682Lithium diisopropylamideHCID 58784445Tert-butyl 3,3-dimethoxycyclopentanecarboxylate

生成物 1

HCID 58987981Tert-butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a cooled (−78° C.) solution of LDA (1.5M in cyclohexane, 41 mL, 61 mmol) in THF (150 mL) was added dropwise over 10 min tert-butyl 3,3-dimethoxycyclopentanecarboxylate (9.37 g, 40.7 mmol) in 25 mL of THF. The resulting mixture was stirred at −78° C. for 30 min, then was treated dropwise with 2-iodopropane (16.3 mL, 163 mmol). After stirring for an additional 10 min, the reaction mixture was permitted to warm to rt. After stirring overnight, the reaction mixture was diluted with ether and washed with brine. The ethereal layer was dried over anhydrous MgSO4, filtered, and concentrated. After storing the crude product under vacuum overnight, it was purified by MPLC (silica, 20% ethyl acetate/hexane) to give tert-butyl 1-isopropyl-3,3-dimethoxycyclopentanecarboxylate. 1H NMR (500 MHz, CDCl3) δ 3.21 (s, 3H), 3.18 (s, 3H), 2.56 (app d, J=14 Hz, 1H), 2.26 (m, 1H), 1.78-1.89 (m, 3).

後処理

  1. stirringAfter stirring for an additional 10 min
  2. temperatureto warm to rt
  3. stirringAfter stirring overnight
  4. washwashed with brine
  5. dry with materialThe ethereal layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customunder vacuum overnight, it
  9. customwas purified by MPLC (silica, 20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-aa73de7001d0447a88e7b3a9ba1e5879
出典データセット
uspto-grants-2010_04
特許番号
US07700591B2

反応ノート

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