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

HRID 1090352Notes

Reaction equation

HRID 1090352 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N12CCCN=C1CCCCC2.[NH2:20][CH2:21][CH2:22][CH2:23][OH:24]>ClCCl>[O:24]([CH2:23][CH2:22][CH2:21][NH2:20])[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 11074190(3-Aminopropoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyldimethylsilyl chloride (14.7 g, 97.5 mmol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (14.6 ml, 97.5 mmol) was added to a solution 3-amino-1-propanol (7.45 ml, 97.5 mmol) in dichloromethane (100 ml) at 0° C. under argon. After 6 hours stirring at room temperature, the mixture was quenched with water and washed successively with 10% hydrochloric acid, saturated sodium bicarbonate solution and brine. Evaporation of the dried (magnesium sulfate) organic phase gave the title amine. 1 (HNMR(CDCl3): -0.03 (s, 6H), 0.81 (s, 9H), 1.61 (p, 2H, J=6.1 Hz), 2.20 (br, 2H), 2.75 (t, 2H, J=6.8 Hz) and 3.63 (t, 2H, J=6.12 Hz).

Workup

  1. customthe mixture was quenched with water
  2. washwashed successively with 10% hydrochloric acid, saturated sodium bicarbonate solution and brine
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate) organic phase

Sources & evidence

ORD record
ord-34bc7f199fc344b58ce7fa5fa78be694
Source dataset
uspto-grants-1992_01
Patent number
US05081261

Reaction notes

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