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

HRID 1518951Notes

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

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).

Workup

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

Sources & evidence

ORD record: ord-948b7050c31d4a639642eafa35ff2efa
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073856B2

Reaction notes

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