Potassium Carbonate → HCID 58181382, compound

HRID 876601Notes

Reaction equation

HRID 876601 reaction equation
[OH:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][NH:12][C:11]1=[O:16])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[F:17][C:18]([F:27])([F:26])[C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].CN(C)[C@@H]1CCCC[C@H]1N>O1CCCCO1.[Cu]I>[OH:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:27])([F:26])[F:17])=[CH:20][CH:21]=2)[C:11]1=[O:16])[C:3]([O:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:4]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 58181397HCID 58181397, compound

Product 1

HCID 58181382HCID 58181382, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1385701,2-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

(R)-tert-butyl 2-hydroxy-2-((R)-3-oxomorpholin-2-yl)acetate (0.5 g, 0.002162 mol) and 4-trifluoromethylphenyl iodide (0.882 g, 1.5 eq) were dissolved in 1,2-dioxane (14 ml), to this mixture were added CuI (82 mg, 0.2 eq), K2CO3 (598 mg, 2 eq), and trans-N,N-dimethylcyclohexane-1,2-diamine (0.1 ml, 0.3 eq). The resulting solution was degassed and heated at 115° C. for 5 hours. The mixture was cooled to rt, the solid removed by filtration, solution washed with water, dried (MgSO4), and concentrated. The resulting residue was then purified by silica gel chromatography (0-20% EtOAc in hexane) to give 477 mg of compound 93-1.

Workup

  1. customThe resulting solution was degassed
  2. temperatureThe mixture was cooled to rt
  3. customthe solid removed by filtration, solution
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe resulting residue was then purified by silica gel chromatography (0-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-0f1255d7bcd846358eb20bbcfb79b548
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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