Tetrahydrofuran → (R)-2-Methyl-propane-2-sulfinic acid [(R)-1-(4-chloro-3,5-dimethyl-phenyl)-2-methyl-propyl]-amide
Reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](/[CH:9]=[N:10]/[S@@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])=[CH:4][C:3]=1[CH3:17].[CH2:18]1[CH2:22]OC[CH2:19]1>>[Cl:1][C:2]1[C:3]([CH3:17])=[CH:4][C:5]([C@H:9]([NH:10][S@@:11]([C:13]([CH3:14])([CH3:16])[CH3:15])=[O:12])[CH:18]([CH3:22])[CH3:19])=[CH:6][C:7]=1[CH3:8]Participants
3
Procedure
In a separate flask a solution of imine INT 36 (5 g, 18.4 mmol) in THF (140 mL) was cooled in a dry ice bath under argon to −78° C. At this temperature the organozincate solution from above was added dropwise over a period of about 30 minutes. Stirring was continued for another hour before the resulting mixture was first quenched carefully with 10% ammonium chloride solution (40 mL), then water (50 mL). The reaction mixture was allowed to warm up to room temperature and was then extracted with Et2O (3×). The organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/EtOAc).
Workup
- additionAt this temperature the organozincate solution from above was added dropwise over a period of about 30 minutes
- waitwas continued for another hour before the resulting mixture
- customwas first quenched carefully with 10% ammonium chloride solution (40 mL)
- extractionwas then extracted with Et2O (3×)
- washThe organic layers were washed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude was purified by chromatography on silica gel (cyclohexane/EtOAc)
Sources & evidence
- ORD record
- ord-eaf7e1efb7a043b3821ef7af46f84a11
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791100B2
Reaction notes
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