Ethyl Acetate → HCID 86674686、化合物

HRID 571826ノート

反応式

HRID 571826 の反応式
[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]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 71743185Tert-butyl 2-(4-amino-3-bromophenyl)morpholine-4-carboxylateHCID 178418546HCID 178418546、化合物

生成物 1

HCID 86674686HCID 86674686、化合物収率 21%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
160 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-a41539506d724a53a24a7d5d7d2bdde8
出典データセット
uspto-grants-2015_05
特許番号
US09029370B2

反応ノート

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