Tyramine → tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

HRID 587939Notes

Reaction equation

HRID 587939 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[OH-].[Na+].[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O.C([O-])(O)=O.[Na+]>O1CCOCC1>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][C:14](=[O:13])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5610TyramineHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
22 °C

Procedure

To a solution of 1.00 g (5.75 mmol) of 4-(2-aminoethyl)phenol in 5 mL of dioxane at 22° C. was added 2 mL of 1 N NaOH followed by 1.88 g (8.62 mmol) of BOC2O dissolved in 2 mL of dioxane. The mixture was stirred at 22° C. for 2 h and then neutralized by adding 25 mL of saturated NaHCO3 which resulted in a pH of about 7.5-8. The aqueous layer was separated and extracted with DCM (3×50 mL). The organics were combined, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel eluting with a mixture of hexane and ethyl acetate to give tert-butyl 4-hydroxyphenethylcarbamate as a colorless oil.

Workup

  1. customresulted in a pH of about 7.5-8
  2. customThe aqueous layer was separated
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel eluting with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-4fc82679229e4655969ca4afaf2ec05d
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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