Tetrahydrofuran → 4-(Tert-butyldimethylsilyloxy)benzyloxyamine

HRID 2299749Notes

Reaction equation

HRID 2299749 reaction equation
O.NN.[Si:4]([O:11][C:12]1[CH:30]=[CH:29][C:15]([CH2:16][O:17][N:18]2C(=O)C3=CC=CC=C3C2=O)=[CH:14][CH:13]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Si:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][O:17][NH2:18])=[CH:29][CH:30]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 11825150N-[4-(tert-butyldimethylsilyloxy)benzyloxy]phthalimide

Product 1

HCID 118211174-(Tert-butyldimethylsilyloxy)benzyloxyamineYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Hydrazine monohydrate (1.25 ml) was added to a solution of N-[4-(tert-butyldimethylsilyloxy)benzyloxy]phthalimide (5.00 g) in ethanol (10 ml)-tetrahydrofuran (40 ml) and stirred at 60° C. for 1 hour. The reaction mixture was cooled to room temperature, an aqueous solution of potassium carbonate was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated to obtain 4-(tert-butyldimethylsilyloxy)benzyloxyamine (3.15 g, yield 95%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89881f9db590407d98a9ce1cf7ffdc4c
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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