Methyl chloroformate → (R)-methyl 1-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1792097Notes

Reaction equation

HRID 1792097 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH3:6][O:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@@H:10]([NH2:18])[C:9]1=[O:19].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O.CCCCC>[CH3:6][O:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@@H:10]([NH:18][C:2](=[O:3])[O:4][CH3:5])[C:9]1=[O:19]

Participants

7

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 54379478HCID 54379478, compound

Product 1

HCID 10538623(R)-methyl 1-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamateYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8003PentaneSolvent

Procedure

A solution of methyl chloroformate (42.8 g, 0.453 mol) in chloroform (50 ml) was added to a mixture of (R)-1,2,3,4-tetrahydro-1-methoxy-2-oxo-3-quinolinamine 1 (M. Kawase, T. Kitamura, Y. Kilugawa, J. Org. Chem., 54, 1989 3394–3403)(0.15 mol) and sodium bicarbonate (50.4 g, 0.600 mol) in chloroform (250 ml) and water (100 ml) over a period of 10 minutes at 0° C. The mixture was stirred overnight at room temperature, diluted with pentane, and the layers were separated. The aqueous layer was extracted with diethylether, and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave an amber oil. Purification by flash chromatography (230–400 mesh silica gel, 35–40% ethyl acetate in hexane) gave the title compound as a light yellow oil (37.0 g, 99%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with diethylether
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under vacuum
  6. customto leave an amber oil
  7. customPurification by flash chromatography (230–400 mesh silica gel, 35–40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-52b64d49f97e460aaf28e0d6614f1d05
Source dataset
uspto-grants-2006_07
Patent number
US07074927B2

Reaction notes

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