Imidazole → HCID 66783809, compound

Participants

Reaction Steps

Triethylchlorosilane (351 mg, 2.33 mmol) was added to a solution of [(R)-2-hydroxy-3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-carbamic acid benzyl ester (260 mg, 0.78 mmol), imidazole (264 mg, 3.89 mmol), and 4-(dimethylamino)pyridine (1.9 mg, 16 μmol) in N,N-dimethylformamide at RT, then after 90 min the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 7:3) afforded the title compound (397 mg, 91%). Light yellow liquid, MS: 563.4 (M+H)+.

Provenance & Evidence