Methylamine → 4-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide

HRID 1784506노트

반응식

HRID 1784506 반응식
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]12[CH2:15][CH2:14][C:11]([C:16]([OH:18])=O)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)(=[O:5])=[O:4])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:25][NH2:26]>C(Cl)Cl.CN(C=O)C>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]12[CH2:15][CH2:14][C:11]([C:16]([NH:26][CH3:25])=[O:18])([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)(=[O:5])=[O:4])[CH3:2]

참가 물질

6

반응물 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 225917104-[2-(Ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylic acid

생성물 1

HCID 207550374-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

Carboxylic acid 10-4 (810 mg, 2.96 mmol) was dissolved in 12 mL of anhydrous methylene chloride under nitrogen atmosphere, treated with oxalyl chloride (2M in methylene chloride, 4.4 mL, 8.8 mmol) and subsequently with 5 drops of DMF. The reaction was stirred at room temperature under nitrogen atmosphere for 90 min, then evaporated and placed under vacuum for 20 min. The acid chloride was dissolved in anhydrous methylene chloride (12 mL), cooled in an ice-bath, and then treated dropwise with a solution of methylamine (2M in THF, 8.9 mL, 17.8 mmol). Upon addition of the amine, the cooling bath was removed and the reaction stirred at ambient temperature for 30 min. The mixture was diluted with 200 mL of methylene chloride and washed with 1N aqueous HCl, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated. The residue was subjected to chromatography on silica gel eluting with a gradient from 0 to 3.5% methanol in methylene chloride to give 4-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide 10-5 as a white powder. MS (ESI+)=288 (M+1).

후처리

  1. customevaporated
  2. waitplaced under vacuum for 20 min
  3. dissolutionThe acid chloride was dissolved in anhydrous methylene chloride (12 mL)
  4. temperaturecooled in an ice-bath
  5. customthe cooling bath was removed
  6. stirringthe reaction stirred at ambient temperature for 30 min
  7. additionThe mixture was diluted with 200 mL of methylene chloride
  8. washwashed with 1N aqueous HCl, saturated aqueous sodium bicarbonate, and brine
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. customevaporated

출처 및 근거

ORD 기록
ord-e706c624ca62436c8ab912eeec11dc73
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504402B2

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