Potassium Carbonate → 1-tert-Butyl 3-methyl 4-(1-benzhydrylazetidin-3-yl)piperazine-1,3-dicarboxylate

HRID 588888노트

반응식

HRID 588888 반응식
CS(O[CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[N:23]1([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28][CH2:27][NH:26][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:24]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:10]([N:8]1[CH2:9][CH:6]([N:26]2[CH2:27][CH2:28][N:23]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:24][CH:25]2[C:29]([O:31][CH3:32])=[O:30])[CH2:7]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27568191-tert-Butyl 3-methyl piperazine-1,3-dicarboxylateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

생성물 1

HCID 904616531-tert-Butyl 3-methyl 4-(1-benzhydrylazetidin-3-yl)piperazine-1,3-dicarboxylate수율 52.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1-benzhydrylazetidin-3-yl methanesulfonate (2.4 g, 7.56 mmol), tert-butyl methyl piperazine-1,3-dicarboxylate (1.85 g, 7.56 mmol), K2CO3 (1.6 g, 11.34 mmol) in CH3CN (40 mL) was stirred at reflux for 16 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10% petroleum ether/ethyl acetate) to afford the desired product (1.85 g, 51% yield).

후처리

  1. temperatureat reflux for 16 h
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (10% petroleum ether/ethyl acetate)

출처 및 근거

ORD 기록
ord-bc5901fd68ae4e54a16b37ff607c048f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227978B2

반응 노트

불러오는 중…