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

HRID 643523노트

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HRID 643523 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-aa73de7001d0447a88e7b3a9ba1e5879
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700591B2

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