Sodium Carbonate → HCID 17819201, compound

HRID 1988299Notes

Reaction equation

HRID 1988299 reaction equation
[NH2:1][C@H:2]([C:15]([O:17]C)=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[C:19](=O)([O-])[O-].[Na+].[Na+].C(Cl)(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCOCC1.O.C1COCC1.O>[C:11]([C:6]1[CH:5]=[C:4]([CH2:3][CH:2]([NH:1][CH3:19])[CH2:15][OH:17])[CH:9]=[CH:8][C:7]=1[OH:10])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 15549498Tyr(3-tBu)-OMeHCID 21226445Aluminium lithium hydride

Product 1

HCID 17819201HCID 17819201, compoundYield 67.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of Tyr(3-tBu)-OMe (3.0 g, 11.9 mmol) in 1,4-dioxane/water (12 ml/12 ml), sodium carbonate (1.9 g, 17.9 mmol) and then ethyl chlorocarbonate (1.26 ml, 13.1 mmol) were added under cooling with ice and stirred for 2 hours. The reaction mixture was mixed with water, extracted with chloroform, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure. To a solution of the thus obtained residue (3.85 g) in THF (120 ml), lithium aluminum hydride (2.83 g, 59.7 mmol) was added little by little and stirred at 60° C. for 5 hours. The reaction mixture was poured into ice water, stirred and then filtered with Celite for removing insoluble material. The filtrate was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (methylene chloride:methanol=3:1), giving 3-(3-tert-butyl-4-hydroxyphenyl)-2-methylaminopropanol (T23) (1.9 g, 67%, in 2 steps).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under reduced pressure
  6. stirringstirred at 60° C. for 5 hours
  7. stirringstirred
  8. filtrationfiltered with Celite
  9. customfor removing insoluble material
  10. extractionThe filtrate was extracted with ethyl acetate
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-592152821e2047d9aaf9bebeb40ea176
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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