Diisobutylaluminumhydride → [(1S)-1-[(2S,4R)-5-hydroxy-4-methyl-tetrahydrofuran-2-yl]propyl] benzoate

HRID 60744Notes

Reaction equation

HRID 60744 reaction equation
[C:1]([O:9][C@H:10]([C@@H:13]1[CH2:17][C@@H:16]([CH3:18])[C:15](=[O:19])[O:14]1)[CH2:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[C:1]([O:9][C@H:10]([C@@H:13]1[CH2:17][C@@H:16]([CH3:18])[CH:15]([OH:19])[O:14]1)[CH2:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 121396370HCID 121396370, compound2×

Product 1

HCID 121396392[(1S)-1-[(2S,4R)-5-hydroxy-4-methyl-tetrahydrofuran-2-yl]propyl] benzoateYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of [(1S)-1-[(2S,4R)-4-methyl-5-oxo-tetrahydrofuran-2-yl]propyl] benzoate (compound 28h, 1.3 g, 5.0 mmol) in THF (100 mL) was added diisobutyl aluminium hydride (11 mL, 11 mmol) dropwise at −78° C. and the mixture was stirred at −78° C. for 2 hours. The mixture was quenched by saturated NH4Cl solution (5 mL) and extracted with EtOAc (100 mL) twice. The organic layers were combined, washed with brine (50 ml), dried over Na2SO4 and concentrated in vacuo to afford 1.2 g crude product of [(1S)-1-[(2S,4R)-5-hydroxy-4-methyl-tetrahydrofuran-2-yl]propyl] benzoate (compound 28i), which was used in next step without further purification.

Workup

  1. customThe mixture was quenched by saturated NH4Cl solution (5 mL)
  2. extractionextracted with EtOAc (100 mL) twice
  3. washwashed with brine (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fc45540a88b4da78a4c3efe2500005f
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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