Hydrochloric Acid → HCID 96398683, compound

Participants

Reaction Steps

10% Pd/C (1 g) was added to a solution of 1-(1-phenyl-ethyl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid methyl ester (Diastereomer B, 4.9 g, 17.9 mmol), ammonium formate (5.6 g, 89 mmol) and 5N hydrochloric acid (4.0 ml, 20 mmol) in methanol (180 ml) at room temperature under nitrogen. The mixture was stirred and heated at reflux for 1 hour. Upon cooling the catalyst was removed by filtration through celite (washing with methanol). The filtrate was evaporated and the residue was partitioned between dichloromethane and saturated aqueous potassium carbonate. The aqueous layer was further extracted with dichloromethane (×1) and n-butanol (×1). The combined extracts were evaporated, and the residue was purified by chromatography on silica gel eluting with CH2Cl2 /MeOH/NH3 (80:8:1) to give the title amine (2.7 g, 89%) as a pale yellow oil; δ (360 MHz, d6 -DMSO) 1.50-1.58 (1H, m), 1.76-1.86 (1H, m), 2.66 (1H, br s), 2.76-2.88 (2H, m), 3.04-3.08 (1H, m), 3.10 (1H, br s, NH), 3.18 (1H, dd, J=11.4, 2.5 Hz), 3.40-3.52 (2H, m), 3.56 (3H, s, CO2Me), 3.66 (1H, br s).

Provenance & Evidence