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

HRID 1518951

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

Mix 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. Then charge the reactor with carbon monoxide (50 psi) and stir the mixture at 90° C. for 15 hours. Cool the reactor to ambient temperature, filter over Celite® pad and wash with DCM (150 mL). Sequentially wash the filtrate with water then brine (2×80 mL). Concentrate the organic filtrate under vacuum to obtain the residue as an orange oil. Purify the crude by silica gel flash chromatography eluting with hexane/ethyl acetate (0 to 30% ethyl acetate) 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 over Celite® pad
washwash with DCM (150 mL)
washSequentially wash the filtrate with water
concentrationConcentrate the organic filtrate under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-948b7050c31d4a639642eafa35ff2efa
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09073856B2

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