(R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine → (R)-5-(2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

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Reaction Steps

To a solution of (R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (750 mg, 2.24 mmol, Eq: 1.00) in methanol (150 ml) and 7 M ammonia in methanol (959 μl, 6.71 mmol, Eq: 3) at room temperature added Pd/C (238 mg, 224 mmol, Eq: 0.1) and the mixture was hydrogenated at room temperature for 2 hours. Extracted with dichloromethane and some 25% ammonium hydroxide solution. Dried the organic layer over Na2SO4, filtered off and evaporated totally, dried in HV to give the (R)-5-(2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (497 mg, 1.94 mmol, 86.7% yield) as a white foam. MS (ISP): m/z=257.1 [M+H]+.

Provenance & Evidence