Ethyl Acetate → HCID 86674686, 화합물

HRID 571826노트

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HRID 571826 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1Br.[C:22]([Cu])#[N:23].CCOC(C)=O>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[C:22]#[N:23]

참가 물질

5

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HCID 8857Ethyl AcetateHCID 71743185Tert-butyl 2-(4-amino-3-bromophenyl)morpholine-4-carboxylateHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 86674686HCID 86674686, 화합물수율 21%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
160 °C

실험 절차

To a stirred solution of tert-butyl (RS)-2-(4-amino-3-bromophenyl)morpholine-4-carboxylate (3.76 g) in NMP (30 ml) was added CuCN (1.77 g) and the reaction mixture was then stirred at 160° C. for 5 h. The mixture was then cooled to room temperature and poured into EtOAc. The resulting suspension was filtered through sintered glass and the filtrate was extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane) to afford tert-butyl (RS)-2-(4-amino-3-cyanophenyl)morpholine-4-carboxylate (659 mg, 21%) as a yellow solid. MS (ISP): 321.2 ([M+NH4]+), 304.2 ([M+H]+).

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe resulting suspension was filtered through sintered glass
  3. extractionthe filtrate was extracted sequentially with water and with saturated brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-a41539506d724a53a24a7d5d7d2bdde8
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029370B2

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