Imidazole → HCID 66783503, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-carbamic acid benzyl ester (examples 74/75A; 3.90 g, 12.2 mmol in N,N-dimethylformamide (50 mL) was added tert-butyl-dimethylchlorosilane (2.77 g, 18.3 mmol), imidazole (2.08 g, 30.6 mmol), and 4-(dimethylamino)pyridine (14 mg, 0.12 mmol) at RT. The reaction mixture was heated at 60° C. for 24 h, then partitioned between sat. aq. NaHCO3 solution and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc/MeOH 19:1) afforded the title compound (4.34 g, 82%). Light yellow oil, MS: 433.4 (M+H)+.

Provenance & Evidence