2-(Methylamino)ethanol → N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine

HRID 58206Notes

Reaction equation

HRID 58206 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].CCN(C(C)C)C(C)C.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].CCOCC.O>C(Cl)Cl>[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 80162-(Methylamino)ethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 21584184Diethylether water

Product 1

HCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamineYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(methylamino)ethanol (1.0 g, 13.3 mmol) was stirred in DCM (25.0 ml) under atmosphere of nitrogen. DIEA (3.23 ml, 18.6 mmol) followed by tert-butylchlorodimethylsilane (2.0 g, 13.3 mmol) was added and the reaction mixture was stirred at room temperature over night. The reaction mixture was poured into ether/water. The aqueous layer was extracted with ether three times. The combined organic layer was dried over MgSO4 and evaporated and remaining material was dried under high vacuum to afford title compound (1.4 g, yield: 56%). 1H-NMR (400 MHz, CDCl3) δ 0.08 (s, 6H) 0.91 (s, 9H) 1.93 (br. s., 1H) 2.48 (s, 3H) 2.71 (t, 2H) 3.75 (t, 2H).

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with ether three times
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. customevaporated
  5. customwas dried under high vacuum

Sources & evidence

ORD record
ord-fc05b04f677e40c5994d7bc155187ab9
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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