Tetrabutylammonium Fluoride → 3-Hydroxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine

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Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine (1.49 g, 3.23 mmol) (obtained as described in Reference Example 72(1)) in anhydrous tetrahydrofuran (75 ml) was added a solution of 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (3.88 ml, 3.88 mmol) in an ice bath and the mixture was stirred in an ice bath for 1 hour. After checking the completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (95:5→9:1) as the eluant to afford 3-hydroxy-1-[4-(3-methoxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine (486 mg, yield 60%) as a white solid.

Provenance & Evidence