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

HRID 1755676ノート

反応式

HRID 1755676 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-25eec66906604738af32a65706d512c2
出典データセット
uspto-grants-1995_08
特許番号
US05438045

反応ノート

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