Diisobutylaluminumhydride → HCID 57805786, compound

HRID 2104205Notes

Reaction equation

HRID 2104205 reaction equation
[F:1][CH2:2][C@@H:3]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[CH2:4][C:5](OCC1C=CC=CC=1)=[O:6].[H-].C([Al+]CC(C)C)C(C)C>CCOCC>[F:1][CH2:2][C@@H:3]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[CH2:4][CH:5]=[O:6]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 57805725HCID 57805725, compound

Product 1

HCID 57805786HCID 57805786, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of (S)-benzyl 4-fluoro-3-(1,3-dioxoisoindolin-2-yl)butanoate (19-4, 0.5 mmol) in dry ether (5 ml) was added dropwise 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 19-5 was used in the next reaction step.

Workup

  1. customAfter completion, the reaction was quenched
  2. additionby adding water (10 ml) at −78° C
  3. extractionExtracted with ethyl acetate
  4. washwashed with water (×3), brine (×2)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product 19-5 was used in the next reaction step

Sources & evidence

ORD record
ord-7ea1eede395140dcbf9fa24685813794
Source dataset
uspto-grants-2009_08
Patent number
US07576221B2

Reaction notes

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