Ethylenediamine → HCID 58495532, compound

Participants

Reaction Steps

Add borane-dimethylsulfide complex (6.9 mL, 13.7 mmol, 2M solution in THF) to a solution of 5-cyclopentylthiomethyl-pyridine-2-carbonitrile (1 g, 4 mmol) in THF (12 mL) at room temperature under a nitrogen atmosphere. Stir the solution at room temperature for 16 h. Concentrate the solution in vacuo, dissolve the residue in chloroform (50 mL), add ethylenediamine (0.72 g, 12 mmol) and stir at 50° C. for 1 h. Wash the mixture with water (10 mL), dry the organic phase over Na2SO4 and concentrate in vacuo. Purify the residue by SCX chromatography followed by chromatography on silica gel (10 g) eluting with DCM/2M ammonia in methanol (1:0 to 9:1 gradient) to obtain the title compound (0.24 g, 27%). MS (ES+) m/z: 223.1 (M+H)+.

Provenance & Evidence