Tetrahydrofuran → (S)-4-Benzyl-3-(4-methylpentanoyl)oxazolidin-2-one
Reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C([Li])CCC.[CH3:24][CH:25]([CH3:31])[CH2:26][CH2:27][C:28](Cl)=[O:29].C([O-])(O)=O.[Na+]>CCCCCC>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:28](=[O:29])[CH2:27][CH2:26][CH:25]([CH3:31])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
(S)-4-Benzyl-2-oxazolidinone (15.1 g, 85.0 mmol) was dissolved in THF (200 mL, 2.5 mol), cooled at −78° C. under nitrogen, and stirred for 10 minutes. 1.6 M of n-butyllithium in hexane (53.1 mL) was added dropwise and stirred for 15 minutes. 4-Methylpentanoyl chloride (12.6 g, 93.5 mmol) was added dropwise, stirred for 30 minutes at −78° C., then warmed to 0° C. for 2 hours. 150 mL of saturated NaHCO3 was added and the mixture was warmed to room temperature for 30 minutes. The mixture was extracted with DCM, washed with Na2CO3 (5%) and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Excess oxazolidinone was removed using hexanes to provide intermediate (2a) (14.5 g).
Workup
- stirringstirred for 15 minutes
- stirringstirred for 30 minutes at −78° C.
- temperaturewarmed to 0° C. for 2 hours
- temperaturethe mixture was warmed to room temperature for 30 minutes
- extractionThe mixture was extracted with DCM
- washwashed with Na2CO3 (5%) and saturated aqueous NaCl
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customExcess oxazolidinone was removed
Sources & evidence
- ORD record
- ord-468b70cd3bc54e63b0c1e2c5007f7399
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273008B2
Reaction notes
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