Sodium Hydroxide → 3-Isopropyl-3,7-diazabicyclo[3.3.1]nonane

Participants

Reaction Steps

A 200-mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer, a heating mantle, a condenser with a N2 inlet, and two glass stoppers. To a stirred mixture of amine (30) (5.53 g, 21.4 mmol) and 10% Pd/C (0.64 g, 30 mg/mmol of amine) in CH3OH (80 mL) was added anhydrous HCO2NH4 (3.37 g, 53.5 mmol) in one portion. Stirring the mixture at reflux under N2 for 30 min, cooling the new mixture to RT, and filtering through a celite pad was followed by concentration of the resulting solution to give a viscous oil. The oil was then dissolved in H2O (80 mL) and the pH was adjusted to ~12 by the addition of 10% NaOH. Combined extracts (CH2Cl2, 4×40 mL) of the aqueous solution were dried, filtered, and concentrated (rotary evaporator then vacuum pump, 10 min, RT/0.2 mm Hg) to give amine (31) as a light oil (3.35 g, 93.0%) which was used without further purification. IR (film) cm-1 3315 (N--H), 2965, 2900, 2850, 2790, 2760, 2725 (C--H); 1H NMR (DCCl3) δ1.01 (d, 6H, CH3, J=6.7 Hz), 1.60-1.67 [m, 3H, H(1,5) and H(9)], 2.53-2.59 [m, 3H, ring protons and CH(CH3)2 ], 2.90-3.06 [m, 6H, ring protons], 3.56 (bs, 1H, N--H); 13C NMR (DCCl3) ppm 18.12 (CH3), 30.04 [C(1,5)], 33.62 [C(9)], 52.86 [C(6,8)], 54.59 [CH(CH3)2 ], 54.65 [C(2,4)].

Provenance & Evidence