4-Nitrophenyl chloroformate → HCID 18712733, compound
Reaction equation
[CH3:1][C:2]1([CH3:17])[O:7][CH2:6][C:5](=[O:8])[NH:4][CH:3]1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30]>C1COCC1>[CH3:1][C:2]1([CH3:17])[O:7][CH2:6][C:5](=[O:8])[N:4]([C:29]([O:31][C:32]2[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=2)=[O:30])[CH:3]1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (±)-2,2-dimethyl-3-(3,4-difluorophenyl)-5-oxo-morpholine (240 mg, 0.996 mmol) in THF (10 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1.10 mL, 1.0 M in THF). The mixture was stirred for 30 min at 0° C. and then cooled back to −78° C. The mixture was transferred via a cannula to a precooled solution of 4-nitrophenyl chloroformate (605 mg, 3.0 mmol) in THF (10 mL) at −78° C. The resulting mixture was stirred while warmed to room temperature over 3 hours. The reaction was quenched with water (2 mL) and extracted with EtOAc (2×100 mL). The organic layer was dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography (SiO2, 40:60 EtOAc/Hexanes) to afford 0.328 g (81%) of the product as a pale oil.
Workup
- temperaturecooled back to −78° C
- stirringThe resulting mixture was stirred
- temperaturewhile warmed to room temperature over 3 hours
- customThe reaction was quenched with water (2 mL)
- extractionextracted with EtOAc (2×100 mL)
- dry with materialThe organic layer was dried with Na2SO4
- customthe solvent was evaporated
- customThe residue was purified by column chromatography (SiO2, 40:60 EtOAc/Hexanes)
Sources & evidence
- ORD record
- ord-5143a22747364fd3af86602d9da1a935
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531471B2
Reaction notes
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