Triacetoxyperiodinane → 6-Benzyloxycarbonylamino-8-oxo-5,6,7,8-tetrahydroquinoline

HRID 1765331노트

반응식

HRID 1765331 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:21][CH:20]([OH:22])[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:21][C:20](=[O:22])[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 211070736-Benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinoline

생성물 1

HCID 211070746-Benzyloxycarbonylamino-8-oxo-5,6,7,8-tetrahydroquinoline수율 31%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 6-benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinoline, cis-trans mixture (1.02 g, 3.42 mmol) in methylene chloride (34 mL) at room temperature under nitrogen was added Dess-Martin periodinane (1.73 g, 4.45 mmol). After 2 h, the reaction mixture was diluted with ethyl acetate. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum to yield a residue. The residue was purified by reverse phase preparative HPLC to obtain the title compound (319 mg, 31%) as a brown oil. 13C NMR (400 MHz, CDCl3) δ 194.1, 155.4, 149.8, 147.6, 138.3, 137.2, 136.0, 128.6, 128.3, 128.2, 127.5, 67.0, 46.7, 45.4, 35.4. 1H NMR (400 MHz, CDCl3) δ 8.66 (d, J=4.4 Hz, 1H), 7.61 (d, J=7.9 Hz, 1H), 7.36 (dd, J=4.4, 7.9 Hz, 1H), 7.26 (m, 5H), 5.02 (s, 2H), 4.34 (s, 1H), 3.29 (d, J=15.4 Hz, 1H), 3.04 (d, J=4.0 Hz, 1H), 2.99 (d, J=4.0 Hz, 1H), 2.80 (dd, J=9.2, 11.4 Hz, 1H). HPLC/MS [M+H]+, 297.

후처리

  1. washThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under vacuum
  4. customto yield a residue
  5. customThe residue was purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-df29e8f3adb04b61a8fe1fdcacd55a8d
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226942B2

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