Imidazole → 2-(tert-butyldiphenylsilyloxy)-N-ethylethanamine

HRID 1771172Notes

Reaction equation

HRID 1771172 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].[CH2:24]([NH:26][CH2:27][CH2:28][OH:29])[CH3:25]>C(Cl)Cl>[Si:10]([O:29][CH2:28][CH2:27][NH:26][CH2:24][CH3:25])([C:6]([CH3:9])([CH3:8])[CH3:7])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 80722-(Ethylamino)ethanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 580801592-(tert-butyldiphenylsilyloxy)-N-ethylethanamineYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Imidazole (1.53 g, 22.44 mmol) and a solution of tert-butylchlorodiphenylsilane (4.63 g, 16.83 mmol) in DCM (10 ml) were added sequentially to a solution of 2-(ethylamino)ethanol (1.099 ml, 11.22 mmol) in DCM (30 ml) and the resulting reaction mixture was stirred at room temperature overnight. The mixture was diluted with DCM and washed with 1N aq. NaHSO4 and saturated aq. NaHCO3. The organic layer was dried (Na2SO4), concentrated under reduced pressure to give a residue which was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes) to provide the title compound (2.95 g, yield: 80%).

Workup

  1. customthe resulting reaction mixture
  2. washwashed with 1N aq. NaHSO4 and saturated aq. NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d05dbf30b2df427d893d81ff40dd24cc
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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