Reaction #1983

Reaction equation

compound

1-benzyl-3-trifluoromethylpyrrolidine-3-carboxylic acid

diphenylphosphoryl azide

trimethyl amine

t-butanol

→

title compound

Yield 96.7%

1-benzyl-3-(BOC-amino)-3-trifluoromethylpyrrolidine

Yield 96.7%

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux under N2 for 24 hours
3. 3
   ConcentrationThe mixture was concentrated to dryness
4. 4
   workup.DISSOLUTIONthe residue was dissolved in methylene chloride
5. 5
   WashThe solution was washed with satd
6. 6
   ConcentrationNaHCO3 and water, then concentrated
7. 7
   OtherThe residue was chromatographed on silica gel

Procedure

A mixture of 1.42 g of the compound from step 454a, 1.71 g of diphenylphosphoryl azide, 12.3 g of t-butanol and 0.627 g of trimethyl amine was heated at reflux under N2 for 24 hours. The mixture was concentrated to dryness, and the residue was dissolved in methylene chloride. The solution was washed with satd. NaHCO3 and water, then concentrated. The residue was chromatographed on silica gel to give 1.73 g of the title compound.

Source