Sodium Hydroxide → (E)-3-{1'-phenyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid

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Reaction Steps

(E)-3-{1′-Phenyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (541 mg, 1.43 mmol) was hydrolyzed with NaOH following the procedure described in Example 1, Step A, giving (E)-3-{1′-phenyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid as a white solid (455 mg, 87%). The resulting product was treated with NH2OTHP according to the procedure described in Example 1, Step B, giving (E)-3-{1′-phenyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide as a yellow solid (393 mg, 69%). Finally, the removal of the THP protecting group following the procedure described in Example 2, Step D gave the crude product, which was purified by preparative HPLC giving 50 mg of (E)-3-{1′-phenyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-hydroxy-acrylamide as its trifluoro acetic salt.

Provenance & Evidence