1,4-Dioxaspiro[4.5]decan-8-one → HCID 43168144, compound

Participants

Reaction Steps

A mixture of 4-bromo-2-chloro-phenylamine (6 g, 29.06 mmol), 1,4-cyclohexanedione monoethyleneketal (6.908 g, 43.59 mmol), and sodium triacetoxy-borohydride (9.239 g, 43.59 mmol) in DCE (100 ml) and acetic acid (0.2 ml) was stirred at r.t. for 2 days. The mixture was then filtered through a pad of diatomaceous earth and washed with dichloromethane. The filtrate was washed with NaHCO3 (aqueous sat. solution), sodium chloride (aqueous sat. solution), dried (MgSO4) and evaporated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; DCM/EtOAc 4:1 as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate compound D33 (8.57 g, 85%).

Provenance & Evidence