Phenylethanolamine → HCID 14624895, compound

HRID 649612Notes

Reaction equation

HRID 649612 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-bb8953ea0ad64f54a7d1c5a69ef39598
Source dataset
uspto-grants-1988_04
Patent number
US04740595

Reaction notes

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