Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-:16].[Na+].[Na+].C([SiH](CC)CC)C.[C]=O>CN(C=O)C>[CH:15]([C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1)=[O:16]Participants
Conditions
- Temperature
- 90 °C
Procedure
Combine N-[(1R)-1-(4-bromophenyl)ethyl]-methanesulfonamide (10 g, 35 mmol), (1,1′-bis(diphenylphosphino)-ferrocene)palladium(II) chloride (733 mg, 0.9 mmol), sodium carbonate (3.81 g, 35 mmol) and DMF (50 mL) in a 300 mL PARR reactor. Add triethylsilane (11.6 mL, 0.72 mmol) and purge the reactor with carbon monoxide three times. Charge the reactor with carbon monoxide (50 psi) and stir the mixture at 90° C. for 15 h. Cool the reactor to ambient temperature; open; filter mixture through a Celite® pad; and wash the pad with DCM (150 mL). Sequentially wash the filtrate with water then brine (2×80 mL). Concentrate the organic phase under reduced pressure to obtain the residue as an orange oil. Purify the orange oil by silica gel flash chromatography eluting with hexane/EtOAc (0 to 30% EtOAc) to provide the title compound (5.6 g, 70%, ee>98%). MS (m/z): 228 (M+1).
Workup
- temperatureCool the reactor to ambient temperature
- filtrationfilter mixture through a Celite® pad
- washand wash the pad with DCM (150 mL)
- washSequentially wash the filtrate with water
- concentrationConcentrate the organic phase under reduced pressure
Sources & evidence
- ORD record
- ord-e84f96b910b44827b4ff26260fbc4ed5
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993568B2
Linked notes
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