反应 #2171074

反应方程式

crude material 18a

15-Azido-4,7,10,13-tetraoxapentadecanoic Acid tert-Butyl Ester

→

amine

收率 89.4%

15-Amino-4,7,10,13-tetraoxapentadecanoic Acid tert-Butyl Ester

收率 89.4%

溶剂

ethanol

反应条件

后处理

1. 1
   其他The system was evacuated under vacuum
2. 2
   workup.WAITwas complete after 16 hrs
3. 3
   其他The crude reaction
4. 4
   洗涤rinsing with ethyl acetate
5. 5
   其他The solvent was removed
6. 6
   其他the amine purified on silica gel using
7. 7
   workup.ADDITIONa mixture of 15% methanol and 2.5% triethylamine in methylene chloride as the eluant

实验过程

The crude material 18a (3.0 g, 8.0 mmol) was dissolved in ethanol (20 mL) and 300 mg of 10% Pd/C was added. The system was evacuated under vacuum and placed under 1 atm of hydrogen gas via balloon with vigorous stirring, and repeated 4 times to ensure a pure hydrogen atmosphere. The reaction was then stirred overnight at room temperature. TLC showed that the reaction was complete after 16 hrs. The crude reaction was passed through a short pad of celite rinsing with ethyl acetate. The solvent was removed and the amine purified on silica gel using a mixture of 15% methanol and 2.5% triethylamine in methylene chloride as the eluant to give 2.3 g (85% yield) of the desired amine 19a (FIG. 8). 1H NMR: 1.36 (s, 9H), 2.27 (br s., 2H), 2.42 (t, 2H, J=6.4 Hz), 2.80 (t, 2H, J=5.2 Hz), 3.45 (d, 2H, J=5.2 Hz), 3.51-3.59 (m, 12H), 3.63 (d, 2H, J=6.4 Hz). MS: m/z Calculated: 322.21, Found: 321.97.

来源