Hydrochloric Acid → HCID 22473217, compound

Participants

Reaction Conditions

Reaction Steps

BuLi (6.87 ml of a 1.6 M solution in hexanes, 11.0 mmol) was added dropwise over 2 min to a stirred solution of dimethyl(2-[1,2,4]triazol-1-ylethyl)amine (1.4 g, 10 mmol) in THF (50 ml) at −78° C. under nitrogen. The resulting mixture was stirred at −78° C. for 15 min, then warmed to −40° C. and re-cooled to −78° C. DMF (2.31 ml, 30 mmol) was added and the reaction mixture warmed to room temperature and stirred for 15 min. MeOH was added followed by NaBH4 (567 mg, 15 mmol) and the reaction mixture stirred for 30 min. H2O (10 ml) was added followed by 1N HCl (50 ml). The reaction was left to stand overnight. The solvent was removed under reduced pressure and the aqueous extracted with CH2Cl2 (5×75 ml). The combined organic extracts were washed with brine (25 ml), dried (MgSO4) and concentrated under reduced pressure. The crude residue was azeotroped with xylene (2×100 ml) to yield the alcohol (1.24 g, 73%).

Provenance & Evidence