Water → HCID 18672401, compound

Participants

Reaction Steps

To a stirred solution 2-(1-tert-butyloxycarbonylaminoethyl)-5-chlorobenzylazide from the previous step (0.28 g, 0.90 mmol) in THF (10.0 mL) and water (1 mL) at ambient temperature was added Ph3P (0.29 mg, 1.1 mmol). The mixture was refluxed for 3 h. The reaction was partitioned between Et2O and diluted 1N HCl. The Et2O layer was removed, and the aqueous layer basicified with saturated NaHCO3 solution. The aqueous layer was extracted with Et2O which was separated, dried over anhydrous Na2SO4, and filtered. The filtrate solvent was removed under reduced pressure. 2-(1-(tert-butyloxycarbonylamino)ethyl)-5-chlorobenzylamine was obtained as a pink oil (0.205 g; HPLC RT=2.76 min, method A; 1H NMR, 400 MHz, CDCl3, 7.33 ppm (s, 1H), 7.22 ppm (dd, 2H), 5.2 ppm (br s, 1H), 5.0 ppm (br s, 1H), 4.0 ppm (d, 1H), 3.85 ppm (d, 1H), 1.7 (br s, 1H), 1.4 ppm (s, 12H)).

Provenance & Evidence