1-Bromo-3-chloropropane → HCID 53402737, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask were mixed with stirring azetidin-3-ol hydrochloride (available from Beta Pharma, 250 mg, 2.28 mmol) and 1-bromo-3-chloropropane (719 mg, 4.56 mmol.0) in acetonitrile (5 mL) to the suspension was added Cs2CO3 (1.86 g, 5.7 mmol.50). The mixture was stirred at 25° C. for 18 h, then diluted with 15 mL of EtOAc and filtered to remove solids. Filtrate was evaporated and residue purified by chromatography (40 g column, 50 μm from Analogix, 0 to 5% over 20 min (MeOH containing 10% ammonium hydroxide)/dichloromethane (developing TLC in an iodine chamber) to give 1-(3-chloropropyl)azetidin-3-ol (128 mg, 856 μmol, 37.5%) as a clear dense liquid. 1H NMR (CDCl3) δ: 4.25-4.53 (m, 2H), 3.36-3.68 (m, 4H), 2.82-3.04 (m, 2H), 2.58 (t, J=7.2 Hz, 2H), 1.80 (quin, J=6.8 Hz, 2H).

Provenance & Evidence