Toluene → HCID 68427302, compound

Participants

Reaction Steps

A solution of cyclopropanol in toluene (0.24 mol/L, 0.50 mL; 0.12 mmol) was placed in a reaction container, sodium hydride (0.008 g; 0.20 mmol) was added at room temperature, and the resulting mixture was stirred for 1 hr. A solution of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.2 M) in toluene (0.50 mL; 0.10 mmol), BINAP (0.0022 g; 0.0036 mmol) and Pd2(dba)3 (0.0014 g; 0.0015 mmol) were added in this order, the reaction container was purged with argon and the resulting mixture was stirred at 100° C. for 24 hr with heating. The reaction mixture was cooled to room temperature, water (2 mL) was added, and the resulting mixture was extracted with ethyl acetate (3 mL). The ethyl acetate solvent was evaporated under reduced pressure, the residue was dissolved in DMSO (1 mL), and the solution was purified by preparative HPLC to give the title compound as an N-protected form. TFA (1.5 mL) was added to the protected form, and the resulting mixture was stirred at room temperature for 14 hr. TFA was evaporated under reduced pressure, and the residue was dissolved in water (1 mL). The solution was purified by high polar preparative HPLC to give the title compound as a TFA salt.

Provenance & Evidence