Reaction #42325

Reaction equation

tert-butyl (1S)-1-[(2S)-oxiranyl]-2-phenylethylcarbamate

sodium carbonate

3-(2,4-dimethylphenyl)propylamine

→

tert-butyl (1S,2R)-1-benzyl-3-{[3-(2,4-dimethylphenyl)propyl]amino}-2-hydroxypropylcarbamate

Conditions

Workup

1. 1
   Temperatureis heated
2. 2
   Temperatureat reflux overnight
3. 3
   Concentrationand concentrated under reduced pressure
4. 4
   OtherPurification by flash column chromatography (silica; methylene chloride/methanol/ammonium hydroxide, 98/2/1)

Procedure

A stirred mixture of tert-butyl (1S)-1-[(2S)-oxiranyl]-2-phenylethylcarbamate (V, 247 mg, 0.939 mmol), sodium carbonate (299 mg, 2.82 mmol), and 3-(2,4-dimethylphenyl)propylamine (VI, 628 mg, 2.82 mmol) is heated at reflux overnight. The reaction mixture is cooled to 20-25 degrees C. and concentrated under reduced pressure. Purification by flash column chromatography (silica; methylene chloride/methanol/ammonium hydroxide, 98/2/1) gives tert-butyl (1S,2R)-1-benzyl-3-{[3-(2,4-dimethylphenyl)propyl]amino}-2-hydroxypropylcarbamate (VII), NMR (300 MHz, CD3OD): δ 7.22-7.16, 3.81, 3.18, 2.77, 2.54, 2.15, 2.13, 1.89 and 1.23.

Source