Boc-L-Valine → 6-bromo-2H-spiro[benzofuran-3,1'-cyclopentan]-2-one

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 1-(4-bromophenyl)cyclopentanecarboxylic acid (200 mg, 0.743 mmol), iodobenzene diacetate (359 mg, 1.11 mmol), Boc-L-valine (48.4 mg, 0.223 mmol), potassium acetate (146 mg, 1.49 mmol) and palladium (II) acetate trimer (8.34 mg, 5 mol %). Tert-butanol (7.4 mL) was added and the mixture was heated at 90° C. for 11 hours, then at room temperature for 8 hours. The reaction mixture was concentrated, diluted with DCM and filtered. The residue was purified by flash column chromatography on silica gel to afford 6-bromo-2H-spiro[benzofuran-3,1′-cyclopentan]-2-one 7.51 (75 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C12H1279BrO2: 267.0; found: 267.0.

Provenance & Evidence