Ethanolamine → (2-Aminoethoxy)(tert-butyl)dimethylsilane

HRID 555706Notes

Reaction equation

HRID 555706 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([Si:9]([CH3:12])([CH3:11])Cl)([CH3:8])([CH3:7])[CH3:6].CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:5]([Si:9]([CH3:12])([CH3:11])[O:2][CH2:1][CH2:3][NH2:4])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethanolamine (0.5 mL, 8.1 mmol), tert-butyldimethylchlorosilane (1.42 g, 8.9 mmol), Et3N (1.25 mL, 8.9 mmol) and DMAP (51 mg, 0.41 mmol) in DCM (25 mL) is stirred at RT for 18 h. The reaction mixture is quenched by H2O, DCM is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless oil; ES-MS: M+=176.2; 1HNMR (CDCl3) 3.95-3.85 (m, 2H), 3.15-3.10 (m, 2H), 0.90 (s, 9H), 0.05 (s, 6H), NH2 is missing.

Workup

  1. customThe reaction mixture is quenched by H2O, DCM
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-f89a89b2ce374895a6a0144befa29320
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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