Diisobutylaluminum hydride → HCID 131736323, compound
Reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[F:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH:7]([OH:10])[CH2:8][O:9][C:4]=2[CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
tert-Butyl 7-fluoro-3-oxo-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate (Intermediate 6, 2.22 g, 8.31 mmol) was dissolved in THF (20 mL) and cooled to −78° C. DIBAL-H (1 M in toluene, 10.8 mL, 10.8 mmol) was added at a rate to maintain the reaction temperature at below −70° C., and the reaction was thereafter stirred at −78° C. for 50 min. The cooling was removed and the reaction was quenched with NH4Cl (aq. sat. 10 mL). The mixture was allowed to reach rt. The reaction mixture was diluted with DCM and Rochelle's salt (30% aq., 100 mL) and extracted with DCM (2×100 mL). The organics were combined, washed with brine, dried over magnesium sulphate, filtered through a phase separator and concentrated to give the title compound (2.23 g, 100%) as a white solid.
Workup
- temperatureto maintain the reaction temperature at below −70° C.
- customThe cooling was removed
- customthe reaction was quenched with NH4Cl (aq. sat. 10 mL)
- customto reach rt
- additionThe reaction mixture was diluted with DCM and Rochelle's salt (30% aq., 100 mL)
- extractionextracted with DCM (2×100 mL)
- washwashed with brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered through a phase separator
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-121bd98265864b09abed94207ae95dd3
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394291B2
Reaction notes
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