Acetone → HCID 86747094, compound

Participants

Reaction Steps

A solution of 415.3 g (1.16 mol) of [2S,3S]-2,3bis(((1,1-dimethylethyl)dimethylsilyl) oxymethyl)cyclobutanone, the product of Step 1D, in 540 mL of pyridine is added to 117 g (1.2 equivalents) of methoxylamine hydrochloride. The reaction mixture was stirred mechanically for 1 hour at ambient temperature and checked by TLC on silica gel eluting with 4% acetone in hexane. The reaction mixture was stirred until the starting material was consumed according to TLC analysis, and then it was concentrated in vacuo. The residue was then diluted with ethyl acetate (1 L) and water (0.5 L). The resultant layers were separated and the aqueous layer was extracted with ethyl acetate. The combined ethyl acetate solution was washed twice with water (250 mL) and once with brine (150 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on 1 kg silica gel column eluted with 10% diethyl ether in hexane to give 425 g (94% yield) of the title compound, [α]D @ 25° C.=-25.8° (c 3.36; EtOAc).

Provenance & Evidence