Water → N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine

HRID 2169131Notes

Reaction equation

HRID 2169131 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(N(C(C)C)CC)(C)C.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].O>ClCCl>[Si:19]([O:5][CH2:4][CH2:3][NH:2][CH3:1])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamineYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methylamino-ethanol (18-a) (10 g, 133.13 mmol) in dichloromethane (200 mL) were added diisopropylethylamine (30.8 ml, 186.39 mmol) and tert-butyl-chloro-dimethyl-silane (20.06 g, 133.13 mmol) at room temperature. The mixture was stirred for 16 h. After completion of the reaction, water was added and the mixture was extracted with dichloromethane. The separated organic part was washed with water and was dried over sodium sulfate and concentrated under reduced pressure to get [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amine (8-a) (18 g, 71.39%) as a yellow liquid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe separated organic part was washed with water
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3938262fd9b4e43928cba94db3b3569
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

Loading…