Acetic Acid → HCID 22243005, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-oxazol-2-yl)azetidine (357 g, 0.79 mmol) (obtained as described in Reference Example 21(3)) in benzene (8 ml) was added a solution of 0.67M methylamine-trimethylaluminium in benzene (2.8 ml) at room temperature under an atmosphere of nitrogen. The mixture was stirred in a water bath (60° C.) for 7 hours. After checking the completion of the reaction, 10% aqueous acetic acid solution (10 ml) was added to the reaction mixture in an ice bath, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane:ethyl acetate (5:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-cyano-1,3-oxazol-2-yl)azetidine (130 mg, yield 41%) as a colorless oil.

Provenance & Evidence