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

HRID 880225

반응식

HRID 880225 반응식
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]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 28560458N-[(1R)-1-(4-bromophenyl)ethyl]methanesulfonamideHCID 178418416HCID 178418416, 화합물2회

생성물 1

HCID 86691231(R)-N-(1-(4-formylphenyl)ethyl)methanesulfonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  1. temperatureCool the reactor to ambient temperature
  2. filtrationfilter mixture through a Celite® pad
  3. washand wash the pad with DCM (150 mL)
  4. washSequentially wash the filtrate with water
  5. concentrationConcentrate the organic phase under reduced pressure

출처 및 근거

ORD 기록
ord-e84f96b910b44827b4ff26260fbc4ed5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993568B2

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