Potassium Carbonate → 6-Benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinoline

HRID 1765330Notes

Reaction equation

HRID 1765330 reaction equation
C([O:4][CH:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH:7]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[CH2:19]([O:18][C:16]([NH:15][CH:7]1[CH2:6][CH:5]([OH:4])[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 211070758-Acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline

Product 1

HCID 211070736-Benzyloxycarbonylamino-8-hydroxy-5,6,7,8-tetrahydroquinolineYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 8-acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline, cis-trans mixture (1.73 g, 5.07 mmol) in methanol (16 mL) at room temperature under nitrogen was added 10% aqueous potassium carbonate solution (8 mL, 5.79 mmol). After 24 h, the reaction mixture was diluted with methylene chloride. The organic layer was washed sequentially with saturated aqueous ammonium chloride solution and brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum to obtain the title compound (1.47 g, 97%). Silica gel chromatography (eluted with 5% methanol in chloroform) provided inefficient separation of the cis and trans isomers. The cis isomer eluted first. Stereochemical assignment was made based on NOE experiments. Cis isomer: 13C NMR (400 MHz, CDCl3) δ 156.3, 155.8, 147.5, 138.0, 136.5, 128.5, 128.1, 123.1, 77.4, 67.5, 66.5, 44.4, 35.0. HPLC/MS [M+H]+, 299.

Workup

  1. washThe organic layer was washed sequentially with saturated aqueous ammonium chloride solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-b02e0bff0acf4a5999e12e3e89752451
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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