Hydrochloric Acid → 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

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A solution of racemic 1,1-dimethylethyl{(3R,4S)-1-[(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-3-hydroxy-4-piperidinyl}carbamate (200 mg) in acetic acid (6 ml) was treated with a 4M solution of HCl in 1,4-dioxane (2 ml), stirred 2 h at room temperature and evaporated to dryness. A part solution/part suspension of this material in dichloromethane (8.5 ml) and methanol (1.5 ml) was treated with MP-carbonate resin (obtained from Argonaut Technologies) (1.2 g), stirred for 3 h, filtered and the resin washed well with 1:1 dichloromethane/methanol. The filtrate was evaporated and the residue chromatographed on silica gel, eluting with dichloromethane/methanol/0.88 ammonia (89:11:1.1) to give product (133 mg, 87%).

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