Azetidine → HCID 86643245, compound

Participants

Reaction Conditions

Reaction Steps

2-(2,2,2-Trifluoro-acetyl)-1,2,3,4-tetrahydro-isoquinoline-6-carbaldehyde (7.776 mmol, 1 equiv.) and azetidine (9.331 mmol, 1.2 equiv.) were dissolved in 1,2-dichloroethane (37 ml), and the mixture was stirred for 10 minutes at 25° C. Sodium triacetoxyborohydride (10.89 mmol, 1.4 equiv.) was added, and the reaction mixture was stirred for 16 hours at 25° C. Saturated sodium hydrogen carbonate solution (50 ml) was then added, the phases were separated, and the aqueous phase was extracted with dichloromethane (4×20 ml). The combined organic phases were washed with saturated NaCl solution (1×50 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate/dichloromethane/hexane/methanol/-ammonia (25% aq), 30:10:10:2:0.02). Yield: 1.55 g (67%)

Provenance & Evidence