Dimethyl Sulfate → 1-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

HRID 215948

반응식

HRID 215948 반응식
O=[O+][O-].[CH2:4]([C:7]1([C:23]([O:25][CH3:26])=[O:24])[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1)[CH:5]=C.S(OC)(OC)(=O)=[O:28].C(N(CC)CC)C>C(Cl)Cl>[O:28]=[CH:5][CH2:4][C:7]1([C:23]([O:25][CH3:26])=[O:24])[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH2:9][CH2:8]1

참가 물질

6

반응물 4

HCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 24823OzoneHCID 588931861-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate

생성물 1

HCID 588931821-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ozone was passed through a solution of 1-benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate (10.0 g, 0.0315 mol) in methylene chloride (200.0 mL) at −78° C. until the color of the solution turned to steel blue. The reaction mixture was flushed with an atmosphere of nitrogen. Then to the solution was added dimethyl sulfate (6.0 mL, 0.063 mol) followed by triethylamine (8.8 mL, 0.063 mol). The mixture was stirred at room temperature for overnight, and then concentrated. The residue was dissolved in ethyl acetate, and the resulting solution was washed with saturated NH4Cl solution, NaHCO3 (7.5%), brine, dried over Na2SO4, filtered and concentrated to give 1-benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate.

후처리

  1. customThe reaction mixture was flushed with an atmosphere of nitrogen
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe resulting solution was washed with saturated NH4Cl solution, NaHCO3 (7.5%), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9c088989e27043079fb8bfe344eb42fa
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193207B2

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