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

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Reaction Conditions

Reaction Steps

To a solution of (R)-5-(5-bromo-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (1 g, 2.75 mmol, Eq: 1.00) in methanol (80 ml) and ammonia (7 M in MeOH) (1.18 ml, 8.26 mmol, Eq: 3.0) was added at 23° C. under inert atmosphere Pd/C 10% (293 mg, 275 μmol, Eq: 0.1) and the suspension was set under hydrogen (balloon) and stirred at 23° C. for 2 hours. The catalyst was filtered off, washed three times with methanol and evaporated. The residue was extracted with dichloromethane/sat. NaHCO3-sol. and the organic layer was dried over Na2SO4, filtered and evaporated to give the pure (R)-5-(2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (760 mg, 2.67 mmol, 97.1% yield) as a white solid. MS (ISP): m/z=285.4 [M+H]+.

Provenance & Evidence