Ethyl Acetate → (4S,5R) 4-(3,4-difluorophenyl)-5-hydroxymethyl-oxazolidin-2-one
Reaction equation
C[O:2][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[NH:7][C@H:6]1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1)=O.[BH4-].[Li+].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[F:18][C:13]1[CH:12]=[C:11]([C@H:6]2[C@H:5]([CH2:3][OH:2])[O:9][C:8](=[O:10])[NH:7]2)[CH:16]=[CH:15][C:14]=1[F:17]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (4S, 5R)-4-(3,4-difluorophenyl)-2-oxo-oxazolidine-5-carboxylic acid methyl ester [(200 mg, 0.8 mmol) product of Example 6, Step D] in tetrahydrofuran (10 mL) at 0° C. was added a 2 M solution of lithium borohydride in tetrahydrofuran (0.4 mL, 0.8 mmol). After stirring for 20 min at 0° C., saturated sodium bicarbonate (20 mL) was added and the mixture stirred at ambient temperature for 20 min. Ethyl acetate (50 mL) was added and the layers separated. The organic layer was washed with brine (1×10 mL), dried with magnesium sulfate, filtered and concentrated in vacuo to provide (4S, 5R) 4-(3,4-difluorophenyl)-5-hydroxymethyl-oxazolidin-2-one as a white solid.
Workup
- stirringthe mixture stirred at ambient temperature for 20 min
- customthe layers separated
- washThe organic layer was washed with brine (1×10 mL)
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-685d4f1e105d424fad3c553b291fc134
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06319932B1
Reaction notes
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