1,1-Dimethylethyl 15-azido-4,7,10,13-tetraoxapentadecanoate → tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate

Participants

Reaction Steps

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.

Provenance & Evidence