Reaction #1178415

Reaction equation

(S)-benzyl 4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanoate

compound 7-4

(S)-benzyl 4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanoate

diisobutylaluminum hydride

→

(S)-4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanal

Solvents

ether

Conditions

Workup

1. 1
   OtherAfter completion, the reaction was quenched
2. 2
   workup.ADDITIONby adding water (10 mL) at −78° C
3. 3
   ExtractionExtracted with ethyl acetate
4. 4
   Washwashed with water (×3), brine (×2)
5. 5
   Dryingdried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   OtherThe crude product, compound 7-5, was used in the next reaction step

Procedure

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.

Source