Toluene → 2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline

HRID 52538Notes

Reaction equation

HRID 52538 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[C:14]2[CH:9]([CH2:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH:6]1[C:15]([O:17][CH3:18])=[O:16])=[O:4].[K].[C:22]1(C)C=CC=CC=1.IC>C1COCC1.O>[CH3:22][C:6]1([C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:8][CH:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH2:10]2)[N:5]1[C:3](=[O:4])[C:2]([F:1])([F:19])[F:20]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 5462222PotassiumHCID 86750626HCID 86750626, compound

Product 1

HCID 867506272-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinolineYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline (8.7 g, 30.3 mmol)in THF (100 mL) was added slowly 0.5N potassium hexamethylsilazide in toluene (66.6 mL, 33.3 mmol) over 15 min at -78° C. The mixture was stirred for 10 min followed by addition of iodomethane (2.3 mL, 36.4 mmol) at the same temperature. The mixture was allowed to warm to room temperature, stirred 5 h, poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated to give 8.98 g of 2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline (98%): 1H NMR (270 MHz, CDCl3) δ7.18 (m, 3H), 7.07 (m, 1H), 3.71 (s, 3H), 2.90 (td, 1H, J=13.9, 3.3 Hz), 2.50 (dt, 1H, J=13.9, 3.3 Hz), 2.28 (dt, 1H, J=13.9, 3.3 Hz), 1.56 (s, 3H), 1.53 (td, 1H, J=13.9, 3.3 Hz).

Workup

  1. stirringstirred 5 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0def70cacf644c37aa161d2ee50c0060
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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