Water → HCID 10041705, compound

Participants

Reaction Steps

The crude azide (1.29 g) is dissolved in 7 ml dry tetrahydrofuran, and 0.82 g (3.1 mmol) triphenylphosphine is added followed by two boiling stones and 0.08 ml (4.4 mmol) water. The solution is stirred for 14 h. An additional 0.82 g triphenylphosphine and 0.08 ml water are added and the mixture is stirred for another 5 h. The reaction mixture is concentrated under vacuum and then purified by silica gel chromatography using first ethyl acetate to remove nonpolar impurities and triphenylphosphine oxide. Then the eluent is changed to 9:1 methanol/triethylamine to obtain methyl 8-amino-2,2-dimethyl-4-(3-[3-pyridyl)propyl]-octanoate as an oil; NMR (CDCl3): delta 3.59 (s,3H), 2.67 (t,2H), 2.54 (t,2H), 1.13 (s,6H).

Provenance & Evidence