Hydrochloric Acid → HCID 68626334, compound

Participants

Reaction Steps

3-(t-Butoxycarbonylamino)pyrrolidine (1 g, 1 eq) is dissolved in DMF (15 mL) and NaH 60% in oil (258 mg, 1.2 eq) is added followed by 2-bromoethyl methyl ether (656 μL, 1.3 eq). Water (150 mL) and EtOAc (150 mL) are added and the two layers are separated. The aqueous layer is extracted with EtOAc (2×150 mL). The combined organic layers are washed with brine, dried over MgSO4 filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (100% EtOAc). The isolated compound (300 mg, 23%) is dissolved in dioxane (2 mL) and HCl 4 M solution in dioxane (5 mL, 20 eq) is added. The solution is stirred for 1 h and the reaction mixture is then concentrated and co-evaporated with toluene to afford 1-(2-methoxy-ethyl)-pyrrolidin-3-ylamine 2HCl (266 mg, 100%).

Provenance & Evidence