Sodium Hydroxide → (2-Aminoethoxy)(tert-butyl)dimethylsilane

HRID 2301263Notes

Reaction equation

HRID 2301263 reaction equation
C1(=O)[NH:5]C(=O)C2=CC=CC=C12.[K].Br[CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[OH-].[Na+]>CN(C=O)C>[Si:17]([O:16][CH2:15][CH2:14][NH2:5])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneYield 150.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Nine grams (9 g) of potassium phthalimide was suspended in 100 mL of DMF to which 10 g of 1-bromo-2-t-butyldimethylsilyloxyethane (BrCH2CH2OTBDMS) was added and the mixture heated at 75° C. overnight. The mixture was added to 300 mL of a 5% sodium hydroxide (NaOH) solution and extracted with 300 mL of ether. The ether phase was washed twice with water, dried over Na2SO4 and the solvent removed under reduced pressure. The resulting solid was dissolved in 100 mL of CH3OH, then 3 mL of hydrazine (H2NNH2) was added. After 5 hr, 300 mL ether was added and the organic phase separated from the white precipitate by filtration. Removal of the solvent under reduced pressure yielded 11 g of O-(t-butyldimethylsilyl)ethanolamine. Five grams (5 g) of O (t butyldimethylsilyl)ethanolamine was dissolved in 40 mL of THF and 8 mL of (i-Pr)2NEt. Five milliliters (5 mL) of diphenylphosphinic chloride (Ph2P(O)Cl) was slowly added which produced a white precipitate. After 2 hr, the THF was removed under reduced pressure and the residue dissolved in 200 mL of CH2Cl2. The CH2Cl2 solution was washed with a saturated bicarbonate solution and brine. Removal of CH2Cl2 under reduced pressure followed by flash chromatography on SiO2 gel using CH2Cl2 produced the product (9 g).

Workup

  1. additionwas added
  2. extractionextracted with 300 mL of ether
  3. washThe ether phase was washed twice with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed under reduced pressure
  6. dissolutionThe resulting solid was dissolved in 100 mL of CH3OH
  7. addition3 mL of hydrazine (H2NNH2) was added
  8. addition300 mL ether was added
  9. customthe organic phase separated from the white precipitate by filtration
  10. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-601ed426f6ed4a8683411940bca45903
Source dataset
uspto-grants-2002_12
Patent number
US06500669B1

Reaction notes

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