2-(Ethylamino)ethanol → [2-(tert-Butyldimethylsilanyloxy)ethyl]ethylamine

HRID 1771195Notes

Reaction equation

HRID 1771195 reaction equation
CCN(C(C)C)C(C)C.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].[CH2:18]([NH:20][CH2:21][CH2:22][OH:23])[CH3:19]>C(Cl)Cl>[Si:14]([O:23][CH2:22][CH2:21][NH:20][CH2:18][CH3:19])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 80722-(Ethylamino)ethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 72666539[2-(tert-Butyldimethylsilanyloxy)ethyl]ethylamineYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DIPEA (5.48 ml, 31.38 mmol) and tert-butylchlorodimethylsilane (6.76 g, 22.42 mmol) were added to a solution of 2-(ethylamino)ethanol (1.998 g, 22.42 mmol) in DCM (39.3 ml) at room temperature. The mixture was stirred at room temperature for 20 hours, partitioned between H2O/Et2O (50 ml/50 ml). The aqeuous phase was extracted with ether (3×30 ml). The combined organic layers were concentrated under reduced pressure to give a residue which was re-dissolved in DCM (50 ml), dried (Na2SO4), filtered and concentrated under vacuum to give the title compound (3.9 g, yield: 85%).

Workup

  1. custompartitioned between H2O/Et2O (50 ml/50 ml)
  2. extractionThe aqeuous phase was extracted with ether (3×30 ml)
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. customto give a residue which
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bbb17e50e871486f9825400f391f06c2
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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