2,2,2-Trifluoroethanol → HCID 69833445, compound

HRID 279369Notes

Reaction equation

HRID 279369 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[N:5]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]([C:20](Cl)=[O:21])[CH:8]([CH3:23])[CH2:7]1)[CH3:2].[F:32][C:33]([F:37])([F:36])[CH2:34][OH:35].[H-].[Na+]>O1CCOCC1>[F:32][C:33]([F:37])([F:36])[CH2:34][O:35][C:20]([N:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[C@H:6]([N:5]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:4]([O:3][CH2:1][CH3:2])=[O:31])[CH2:7][C@@H:8]1[CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 54470852HCID 54470852, compound

Product 1

HCID 69833445HCID 69833445, compoundYield 156%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of benzyl-(1-chlorocarbonyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid ethyl ester (Example 107A) (24 mg, 0.054 mmol), 2,2,2-trifluoroethanol (0.10 mL, 1.4 mmol), and sodium hydride (56 mg, 60% dispersion in mineral oil, 1.4 mmol) in anhydrous dioxane (1 mL) was stirred at room temperature overnight. The reaction mixture was quenched with 10 mL of water and extracted with ethyl acetate (3×15 mL). The combined organic phases were washed with 10 ml of brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 43 mg of an oil. Purification by silica gel chromatography using 0-50% ethyl acetate/hexanes as eluent afforded the desired final product (15 mg, 58%): MS m/z 510 (M+), 528 (M++18); 1H NMR (CDCl3) δ6.99 (C8, s, 1H), 6.44 (C5, s, 1H).

Workup

  1. customThe reaction mixture was quenched with 10 mL of water
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. washThe combined organic phases were washed with 10 ml of brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f9fac8036ee4e05a5f867ac1e3c9c4c
Source dataset
uspto-grants-2002_03
Patent number
US06362198B1

Reaction notes

Loading…