3-Amino-1-propanol → (3-Aminopropoxy)(tert-butyl)dimethylsilane

HRID 1920662Notes

Reaction equation

HRID 1920662 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>C1COCC1.C(OCC)C>[C:11]([Si:8]([CH3:10])([CH3:9])[O:5][CH2:4][CH2:3][CH2:2][NH2:1])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 90863-Amino-1-propanolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11074190(3-Aminopropoxy)(tert-butyl)dimethylsilaneYield 91.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.4 g (98 mmol) 3-aminopropanol in 10 ml THF was added at room temperature to a suspension of 4.12 sodium hydride (60%; 103.2 mmol) in 140 ml THF. The mixture was stirred for 1 hour and then 16.28 g (108 mmol) tert-butyl-dimethylsilylchloride was added and vigorous stirring was continued for 1 hour. The mixture was diluted with 300 ml diethylether and washed successively with 100 ml of aqueous K2CO3 (10%), 100 ml of water and 100 ml of brine, dried over MgSO4 and evaporated to give 17 g of light yellow crude product. This product was dissolved in ethyl acetate/hexane 1/10 and filtered through a pad of silica gel. The filtrate was concentrated in vacuo to give 13 g (70%) of the desired product as a colorless oil.

Workup

  1. stirringvigorous stirring
  2. waitwas continued for 1 hour
  3. washwashed successively with 100 ml of aqueous K2CO3 (10%), 100 ml of water and 100 ml of brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-93f49546213c43d6addda70c93725cf9
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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