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

HRID 2038216

Reaction equation

HRID 2038216 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]=O>C([SiH](CC)CC)C.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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 28560458N-[(1R)-1-(4-bromophenyl)ethyl]methanesulfonamideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 86691231(R)-N-(1-(4-formylphenyl)ethyl)methanesulfonamideYield 70.4%

Reagents, catalysts & solvents 2

HCID 12052TriethylsilaneCatalystHCID 6228DimethylformamideSolvent

Procedure

Charge a 300 mL PARR reactor with 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). Add triethylsilane (11.6 mL, 0.72 mmol) and purge the reactor with carbon monoxide three times. Pressurize the PARR reactor with carbon monoxide (50 psi) and stir the mixture at 90° C. for 15 hours. Cool the reactor to ambient temperature; filter through 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 provide an orange oil residue. Purify the residue by silica gel flash chromatography eluting with hexane/EtOAc (0 to 30% EtAc) to provide the title compound (5.6 g, 70%, ee>98%). MS (m/z): 228 (M+1).

Workup

  1. filtrationfilter through Celite® pad
  2. washand wash the pad with DCM (150 mL)
  3. washSequentially wash the filtrate with water
  4. concentrationConcentrate the organic phase under reduced pressure
  5. customto provide an orange oil residue
  6. customPurify the residue by silica gel flash chromatography
  7. washeluting with hexane/EtOAc (0 to 30% EtAc)

Sources & evidence

ORD record
ord-f3bde30ae8e64a0fbe61c42f787704c8
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Linked notes

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