Tetrahydro-4H-pyran-4-one → HCID 43608624, compound

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Reaction Steps

A mixture of 4-bromo-2-chloro-phenylamine (4 g, 19.37 mmol), tetrahydro-4H-pyran-4-one (2.69 ml, 29.05 mmol), oven-dried molecular sieves 4 Å (2 g) and sodium triacetoxyborohydride (6.12 g, 29.05 mmol) in DCE (100 ml) was stirred at r.t. for 72 h. The mixture was filtered through a pad of diatomaceous earth. The diatomaceous earth pad was then washed with DCM. The combined filtrates were washed with NaHCO3 (aqueous saturated solution), dried (Na2SO4) and concentrated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 5%). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D32 as a brown oil (4.83 g, 86%).

Provenance & Evidence