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

HRID 2401475Notes

Reaction equation

HRID 2401475 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[CH3:9][NH:10][CH2:11][CH2:12][OH:13].N1C=CN=C1.O>ClCCl>[Si:5]([O:13][CH2:12][CH2:11][NH:10][CH3:9])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 80162-(Methylamino)ethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamineYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyldimethylchlorosilane (4.2 g, 27.9 mmol) in dichloromethane (10 mL) was added dropwise over 3 min to a stirred solution of 2-(methylamino)ethanol (2.0 g, 26.6 mmol) and imidazole in dichloromethane (20 mL) at room temperature. The resulting mixture was stirred at room temperature for 1 h. Water (20 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane then the combined organic phases were passed through a phase separation cartridge and the solvent removed under reduced pressure to afford a colorless oil (5.10 g, 95%). This was taken through to the next step with no further purification.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. customthe combined organic phases were passed through a phase separation cartridge
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b8e5d385509d448298a373b7660d8fae
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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