benzyl 2-((R)-5-(2H-1,2,3-triazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate → 2-((R)-5-[1,2,3]triazol-2-yl-indan-1-yl)-2,7-diaza-spiro[3.5]nonane

Participants

Reaction Steps

In a Parr® shaker bottle, a solution of benzyl 2-(R)-5-(2H-1,2,3-triazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate (6-1b, 1.20 g, 2.7 mmol) in MeOH (30 mL) was treated with 10% Pd/C (50% wet for safety, 600 mg). The mixture was hydrogenated at 45 psi for 6 hours. The reaction was filtered through a pad of Celite® and concentrated to afford 2-((R)-5-(2H-1,2,3-triazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane as a glass-like solid (690 mg, 82%). MS (ES+) 310.0 (M+H)+. 1H NMR (CD3OD) δ 0.95 (s, 1H), 1.27-1.32 (m 2H), 1.88-1.92 (m, 3H), 2.26-2.30 (m, 1H), 2.97-3.01 (m, 5H), 3.13 (s, 3H), 3.33-3.51 (m, 1H), 4.07 (br s, 1H), 7.50 (s, 2H), 7.90 (s, 3H).

Provenance & Evidence