Tetrabutylammonium Fluoride → HCID 58291972, compound

Participants

Reaction Steps

4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Intermediate 80, 700 mg) was treated with 1.0M TBAF in THF (3.0 ml) for 16 hours. The reaction was concentrated to reduce the volume of THF, then diluted with ethyl acetate. The organic layer was washed once with water followed by brine, then filtered and dried over sodium sulfate. The resulting residue was suspended in a minimum of dichloromethane and the resulting precipitate was isolated by filtration to yield a single diastereomer of 1,4-dihydroxy-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (132 mg). MS MH+ 282.4

Provenance & Evidence