Potassium Hydroxide → HCID 10990898, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of cis-1-[2-(5-[1,2,4]triazol-4-yl-1H-indol-3-yl)-ethyl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid methyl ester (enantiomer B) (1.9 g, 5.0 mmol), hydrazine hydrate (1.2 ml, 25 mmol) and powdered potassium hydroxide (3.4 g, 61 mmol) in dry ethylene glycol (25 ml) was stirred and heated at 100° C. under nitrogen for 16 hours. Upon cooling the mixture was partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane ) and n-butanol (×2). The combined extracts were evaporated and the residue was purified by chromatography on neutral alumina (grade III) (dry loaded), eluting with CH2Cl2 /MeOH/NH3 (95:5:0.5) to give the title amine (1.0 g, 62%) as a pale yellow foam; δ (250 MHz, d6 -DMSO) 1.33-1.48 (1H, m), 1.90-2.04 (1H, m), 2.14-2.26 (1H, m), 2.40 (1H, dd, J=11.8, 4.9 Hz), 2.56-2.96 (11H, m), 3.07 (1H, t, J=7.4 Hz), 7.30 (1H, dd, J=8.6, 2.1 Hz, Ar--H), 7.34 (1H, d, J=2.2 Hz, Ar--H), 7.48 (1H, d, J=8.6 Hz, Ar--H), 7.79 (1H, d, J=2.0 Hz, Ar--H), 9.03 (2H, s, Triazole-H), 11.11 (1H, br s, NH).

Provenance & Evidence