Trifluoroacetic acid → N-benzyloxy-N-(2-methylpropyl)amine

HRID 976626

Reaction equation

HRID 976626 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][N:16]([CH2:24][CH:25]([CH3:27])[CH3:26])C(=O)OC(C)(C)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([O:15][NH:16][CH2:24][CH:25]([CH3:27])[CH3:26])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19967428tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate

Product 1

HCID 19967392N-benzyloxy-N-(2-methylpropyl)amineYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (21 mL, 270 mmol) was added in a single portion to a solution of tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate (7.6 g, 27 mmol) in methylene chloride (21 mL). A spontaneous reflux occurred. The reaction mixture was stirred without external heating for 20 minutes and then concentrated under vacuum at 45° C. Saturated aqueous sodium bicarbonate was added to the residue followed by a quantity of solid sodium bicarbonate sufficient to bring the pH of the reaction mixture up to a value of 9. The mixture was extracted twice with methylene chloride. The extracts were combined, dried over magnesium sulfate then concentrated under vacuum to provide 4.9 g of N-benzyloxy-N-(2-methylpropyl)amine as an oil.

Workup

  1. temperatureA spontaneous reflux
  2. temperaturewithout external heating for 20 minutes
  3. concentrationconcentrated under vacuum at 45° C
  4. additionSaturated aqueous sodium bicarbonate was added to the residue
  5. extractionThe mixture was extracted twice with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-dc8021c5fc3a41f08acdf0f7506a6e60
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Linked notes

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