Hydrochloric Acid → (2R,5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one

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Reaction Steps

Concentrated aq. HCl (71.99 μL, 0.84 mmol) was added to a solution of (5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 9) (314 mg, 0.84 mmol) in DCM (10 mL) at 0° C. Sodium triacetoxyborohydride (533.3 mg, 2.52 mmol) was added in a single portion and the resulting mixture was stirred allowing warming to room temperature. After 90 minutes the reaction was quenched by the addition of sat. aq. Na2CO3 and the resultant mixture was filtered. The phases were separated, the organic layer was dried (Na2SO4) and the solvent was evaporated to afford a brown oil. This was purified using a Biotage SP4 with a 25 g SNAP cartridge, eluting with 0 to 20% MeOH in EtOAc. This gave two products; the first to elute: (2R,5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one (68 mg, 0.1807 mmol, 21.5% yield) was obtained as a yellow oil.

Provenance & Evidence