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

HRID 1518951노트

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HRID 1518951 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

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온도
90 °C

실험 절차

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).

후처리

  1. temperatureCool the reactor to ambient temperature
  2. filtrationfilter over Celite® pad
  3. washwash with DCM (150 mL)
  4. washSequentially wash the filtrate with water
  5. concentrationConcentrate the organic filtrate under vacuum

출처 및 근거

ORD 기록
ord-948b7050c31d4a639642eafa35ff2efa
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073856B2

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