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

HRID 1765331Notes

Reaction equation

HRID 1765331 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-df29e8f3adb04b61a8fe1fdcacd55a8d
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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