Dimethyl Sulfoxide → Benzyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 1464331노트

반응식

HRID 1464331 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28][OH:29])[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH:28]=[O:29])[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13971210Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylate

생성물 1

HCID 22278282Benzyl 4-(2-oxoethyl)piperidine-1-carboxylate수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

159 g of oxalic acid chloride was dissolved in one liter of dichloromethane, in to which 195.8 g of dimethyl sulfoxide was dropped at -67° C. followed by agitation for 30 minutes. Thereafter, 200 ml of dichloromethane dissolving 66 g of 1-benzyloxycarbonyl-4-(2-hydroxyethyl)piperidine was dropped at -67° C. Subsequently, 380 g of triethylamine was dropped at -67° C. followed by agitation for about 1 hour. After removal of the solvent by distillation, ethyl acetate was added and insoluble matters were removed by filtration, and the resultant filtrate was washed with water and dried with anhydrous magnesium sulfate, followed by filtration and removal of the solvent by distillation. The resultant residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:hexane=20:80) to obtain 55.0 g of the captioned compound (yield 84%).

후처리

  1. additionwas dropped at -67° C.
  2. waitfollowed by agitation for about 1 hour
  3. customAfter removal of the solvent
  4. distillationby distillation, ethyl acetate
  5. additionwas added
  6. custominsoluble matters were removed by filtration
  7. washthe resultant filtrate was washed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. filtrationfollowed by filtration and removal of the solvent by distillation

출처 및 근거

ORD 기록
ord-6a05f5c37c184a868fe05b676da4d971
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304553

반응 노트

불러오는 중…