Ammonium formate → 2-(Naphthalene-1-sulfonyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

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A mixture of 6-benzyloxy-2-(naphthalene-1-sulfonyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1,2,3,4-tetrahydroisoquinoline (0.012 g, 0.019 mmol), ammonium formate (0.033 g, 0.52 mmol), and 20% Pd(OH)2/C (0.002 g) in MeOH (10 ml) was refluxed under N2 for 1.5 hr, then filtered to remove the catalyst. The filtrate was evaporated in vacuo to a residue that was suspended in a mixture of H2O (0.4 ml) and sat. NaHCO3 (0.4 ml). The aqueous mixture was extracted with CH2Cl2 (3×0.8 ml), and all of the combined organic solutions were evaporated to give the crude product. Purification by reverse-phase HPLC, eluting with gradient Primesphere C-18HC (3.0 mm×2.0 mm column with 5 m particle size) column, eluting with a linear gradient starting at time 0 min. of H2O:CH3CN:TFA (99.9:0:0.1), increasing to H2O CH3CN:TFA (0:99.9:0.1) at 4 min., detected with a UV detector (300 nM +/−90 nM and 254 nM +/−25 nM), gave an eluent that was evaporated to dryness to give the named product. MS m/e 493 (M++1).

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