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Ethyl Acetate → (4S,5R) 4-(3,4-difluorophenyl)-5-hydroxymethyl-oxazolidin-2-one

HRID 1856660
Notes
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Reaction equation

HRID 1856660 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 57080183(4S,5R)-4-(3,4-difluorophenyl)-2-oxo-oxazolidine-5-carboxylic acid methyl ester2×

Product 1

HCID 57254260(4S,5R) 4-(3,4-difluorophenyl)-5-hydroxymethyl-oxazolidin-2-oneYield 100%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

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 30 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 (180 mg, 0.8 mmol, 100%)

Workup

  1. stirringthe mixture stirred at ambient temperature for 20 min
  2. customthe layers separated
  3. washThe organic layer was washed with brine (1×10 mL)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0530398a9f5447c89ed5567fc5cdd493
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06143750

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes