Trifluoroacetic acid → Racemic 4-{[(3S,4R)-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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Reaction Steps

A solution of racemic 1,1-dimethylethyl{(3S,4R)-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 (15.57 g) in dichloromethane (170 ml) was cooled in ice-water, treated with trifluoracetic acid (137 ml), stirred 1 hour at room temperature and evaporated to dryness. After keeping under high vacuum for 1 hour, the crude material was dissolved in methanol and run through a column of Amberlyst A21 basic resin (500 ml) (Sigma-Aldrich Co.), eluting with methanol. The solution containing the product was evaporated and the residue chromatographed on silica gel, eluting with dichloromethane/methanol/0.88 ammonia (9:1:0.1) to give product (8.96 g, 76%).

Provenance & Evidence