Methanol → 3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (A+-)-
Reaction equation
[CH3:1][C:2]1([CH3:18])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:5]([C:14](OC)=[O:15])[CH2:4][O:3]1.[H-].C([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH:14]([CH:5]1[CH2:4][O:3][C:2]([CH3:18])([CH3:1])[N:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
The 3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (6.42 g, 24.97 mmol) obtained in the above-described reaction was dissolved in toluene (50 ml) and cooled to −78° C.; subsequently, a toluene solution of diisobutylaluminum hydride (0.93 M) was slowly added dropwise. After 30 minutes, methanol was added to the mixture and the reaction was stopped; a 10% potassium sodium tartrate solution (150 ml) was further added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting concentrate was purified by silica gel column chromatography to produce tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (4.22 g, 74% yield).
Workup
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- concentrationThe resulting concentrate
- customwas purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-8010389cc10f4c26ad08b83b7d267152
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093395B2
Reaction notes
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