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

HRID 370040Notes

Reaction equation

HRID 370040 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)[C@H: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])[C@@H: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 88014990HCID 88014990, 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) δ 6.99 (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-3538f7558ad54bc0af4f45232bc7101a
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

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