2-[2-[(Ethoxycarbonyl)amino]ethyl]-6-methoxyphenyl ethyl carbonate → Ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl carbonate

HRID 717364노트

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HRID 717364 반응식
[C:1](=[O:22])([O:19][CH2:20][CH3:21])[O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][NH:13][C:14](OCC)=[O:15]>C(OCC)(=O)C.O>[C:1](=[O:22])([O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]2[C:4]=1[CH2:11][CH2:12][NH:13][C:14]2=[O:15])[O:19][CH2:20][CH3:21]

참가 물질

4

반응물 1

HCID 904111402-[2-[(Ethoxycarbonyl)amino]ethyl]-6-methoxyphenyl ethyl carbonate

생성물 1

HCID 90410952Ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl carbonate

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
142.5 °C

실험 절차

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed polyphosphoric acid (PPA, 150 g). This was followed by the addition of 2-[2-[(ethoxycarbonyl)amino]ethyl]-6-methoxyphenyl ethyl carbonate (20 g, 64.24 mmol, 1.00 equiv) at 145° C. The resulting solution was stirred for 20 min at 140-145° C. The reaction mixture was cooled to room temperature with a water/ice bath. The resulting solution was diluted with 500 mL of ethyl acetate and 500 mL of water. The resulting mixture was washed with 3×300 mL of water. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 1.5 g (9%) of ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl carbonate as a gray solid. MS (ESI) m/z 266 ([M+H]+).

후처리

  1. customInto a 500-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe reaction mixture was cooled to room temperature with a water/ice bath
  4. washThe resulting mixture was washed with 3×300 mL of water
  5. dry with materialThe mixture was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThis resulted in 1.5 g (9%) of ethyl 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinolin-5-yl carbonate as a gray solid

출처 및 근거

ORD 기록
ord-ccca1dc79d4045b9bb751f8226f9a85e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193707B2

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