Phenylethanolamine → HCID 14624895, compound

HRID 1761714Notes

Reaction equation

HRID 1761714 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 dimethylsiloxy1-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-a1e4817cf4c04027a9aa050268ceb0c5
Source dataset
uspto-grants-1989_05
Patent number
US04827006

Reaction notes

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