Tetrahydrofuran → (S)-4-(3-chlorophenyl)oxazolidin-2-one
Reaction equation
Cl.[NH2:2][C@@H:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)[CH2:4][OH:5].[OH-].[K+].C1C[O:18][CH2:17]C1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O.CCOC(C)=O>[Cl:12][C:8]1[CH:7]=[C:6]([C@H:3]2[CH2:4][O:5][C:17](=[O:18])[NH:2]2)[CH:11]=[CH:10][CH:9]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-2-amino-2-(3-chlorophenyl)ethanol hydrochloride (500 mg, 2.40 mmol) in water (12 mL) at 0° C. was added potassium hydroxide (809 mg, 14.4 mmol) followed by THF (12 mL) and the reaction was stirred at 0° C. for 20 minutes. Triphosgene (713 mg, 2.40 mmol) was added and the reaction was stirred at 0° C. for 2 hours. The reaction was poured into EtOAc and the organic phase washed with 1N HCl, 1N NaOH and brine. After drying over MgSO4, concentration yielded (S)-4-(3-chlorophenyl)oxazolidin-2-one (278 mg, 58.5% yield) as an oil.
Workup
- stirringthe reaction was stirred at 0° C. for 2 hours
- washthe organic phase washed with 1N HCl, 1N NaOH and brine
- dry with materialAfter drying over MgSO4, concentration
Sources & evidence
- ORD record
- ord-16a8dd164b1d43bfab7ac930fe96c913
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865726B2
Reaction notes
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