Diethyl Ether → N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine

HRID 548667Notes

Reaction equation

HRID 548667 reaction equation
CCN(C(C)C)C(C)C.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].[CH3:18][NH:19][CH2:20][CH2:21][OH:22].C(OCC)C>C(Cl)Cl.O>[Si:10]([O:22][CH2:21][CH2:20][NH:19][CH3:18])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 80162-(Methylamino)ethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamineYield 100.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

DIPEA (2.45 mL, 14.0 mmol) and tert-butyldimethylsilyl chloride (1.51 g, 10.0 mmol) were added to a solution of 2-(methylamino)ethanol (751 mg, 10.0 mmol) in dry DCM (25 mL) under argon and the reaction mixture allowed to stir at RT for 16 hours. Diethyl ether (50 mL) and water (50 mL) were added to the reaction mixture and the aqueous phase was extracted with diethyl ether (3×30 mL). The combined extracts were dried (MgSO4), filtered and evaporated to give a pale yellow oil which was dried under high vacuum to give the title compound (1.91 g).

Workup

  1. extractionthe aqueous phase was extracted with diethyl ether (3×30 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give a pale yellow oil which
  6. customwas dried under high vacuum

Sources & evidence

ORD record
ord-11898ff37cf34a6fb3edf422f74d571e
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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