Cyanogen Bromide → HCID 58304318, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate Ea3 (R1,2=cyclopropyl, R3=Me): To a solution of {1-[(S)-1-amino-1-(2-fluoro-5-nitro-phenyl)-ethyl]-cyclopropyl}-methanol (0.50 g) in dry THF (20 ml) was added bromocyanogen (0.24 g) and sodium acetate (0.19 g) and the mixture was stirred at 80° C. overnight. The mixture was cooled to 22° C., diluted with HCl in dioxane (4M, 2.4 ml) and stirring was continued for 1 h. The mixture was partitioned between aqueous saturated Na2CO3 and ethyl acetate, the organic layer was dried, evaporated and the residue purified by chromatography over silca-NH2 using ethyl acetate to give (S)-8-(2-fluoro-5-nitro-phenyl)-8-methyl-5-oxa-7-aza-spiro[2.5]oct-6-en-6-ylamine (0.30 g) as a pale yellow solid. MS (ESI): m/z=280.1 [M+H]+.

Provenance & Evidence