反応 #1178415

ord-5eb646a40cdd4eb2b0e6cda40ca21f14

反応方程式

O=C(C[C@@H](CF)N1C(=O)c2ccccc2C1=O)OCc1ccccc1
(S)-benzyl 4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanoate
O=C(C[C@@H](CF)N1C(=O)c2ccccc2C1=O)OCc1ccccc1
compound 7-4
O=C(C[C@@H](CF)N1C(=O)c2ccccc2C1=O)OCc1ccccc1
(S)-benzyl 4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanoate
CC(C)[CH2][Al+][CH2]C(C)C.[H-]
diisobutylaluminum hydride
O=CC[C@@H](CF)N1C(=O)c2ccccc2C1=O
(S)-4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanal

溶媒

反応条件

温度
-78°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他After completion, the reaction was quenched
  2. 2
    workup.ADDITIONby adding water (10 mL) at −78° C
  3. 3
    抽出Extracted with ethyl acetate
  4. 4
    洗浄washed with water (×3), brine (×2)
  5. 5
    乾燥dried over sodium sulfate
  6. 6
    ろ過filtered
  7. 7
    濃縮concentrated
  8. 8
    その他The crude product, compound 7-5, was used in the next reaction step

実験手順

To a stirred solution of (S)-benzyl 4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanoate (compound 7-4, 0.5 mmol) in dry ether (5 mL) was added dropwise to diisobutylaluminum hydride (1.0 M in toluene, 1.5 mmol) at −78° C. The reaction was stirred at −78° C. for approximately 30 min as monitored by LC/MS. After completion, the reaction was quenched by adding water (10 mL) at −78° C. Extracted with ethyl acetate, washed with water (×3), brine (×2), dried over sodium sulfate, filtered and concentrated. The crude product, compound 7-5, was used in the next reaction step.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08129358B2uspto-grants-2012_03