Sodium Carbonate → (R)-N-(1-(4-formylphenyl)ethyl)methanesulfonamide

HRID 880225

Reaktionsgleichung

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]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-e84f96b910b44827b4ff26260fbc4ed5
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08993568B2

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