Diisobutylaluminum hydride → HCID 67445318, compound

HRID 2194879Notes

Reaction equation

HRID 2194879 reaction equation
[Br:1][C:2]1[C:3]([CH2:10][CH2:11][C:12](OCC)=[O:13])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[C:3]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67447857HCID 67447857, compound

Product 1

HCID 67445318HCID 67445318, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To solution of ethyl 3-(5-bromo-2-methoxypyridin-4-yl)propanoate (1 eq.) from step 3 in THF (0.18M) at −78° C. was added DIBAH (2.5 eq.). The reaction mixture was stirred at −78° C. for 30 min then at 0° C. for 2 h. The reaction was quenched with HCl (1N) at 0° C. and then was diluted with Et2O. The organic extract was washed with water, saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 75% in 30 min) afforded the desired compound.

Workup

  1. waitat 0° C. for 2 h
  2. customThe reaction was quenched with HCl (1N) at 0° C.
  3. additionwas diluted with Et2O
  4. extractionThe organic extract
  5. washwas washed with water, saturated NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  10. washeluting with Hex/EtOAc (10 to 75% in 30 min)

Sources & evidence

ORD record
ord-248a7d56d17d4906913682dd0d531b8a
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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