Phenylethanolamine → HCID 14624895, compound

HRID 1534630Notes

Reaction equation

HRID 1534630 reaction equation
[C:1]1([CH:7]([OH:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].CN(C)C(=N)N(C)C>ClCCl>[C:1]1([CH:7]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1000PhenylethanolamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 664601,1,3,3-Tetramethylguanidine

Product 1

HCID 14624895HCID 14624895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-phenyl-2-aminoethanol (5.323 g, 38.80 mmole) in 50 mL dichloromethane was added tert-butyldimethylsilyl chloride (7.030 g, 46.63 mmole) followed, after 15 minutes by tetramethylguanidine (2.430 g, 21.09 mmole). The reaction mixture was stirred at room temperature for 15 minutes and quenched by addition of water (40 mL). Layers were separated. The aqueous phase was extracted with dichloromethane (40 mL). Combined organic phases were washed with brine (2×50 mL), dried over magnesium sulfate and concentrated in vacuo to give crude 2-phenyl-2-tert-butyl dimethylsiloxy-1-ethylamine.

Workup

  1. customquenched by addition of water (40 mL)
  2. customLayers were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (40 mL)
  4. washCombined organic phases were washed with brine (2×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ec93f2e623b4c4bb548cf2b056b38b5
Source dataset
uspto-grants-1992_02
Patent number
US05089609

Reaction notes

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