Methanol → HCID 68380511, compound

Participants

Reaction Conditions

Reaction Steps

184 mg (0.39 mmol) of (2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid [6′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-3,4,5,6-tetrahydro-2H-1,2′-bipyridinyl-4-yl]amide was dissolved in 5 ml of THF, and 579 μl of 2M borane dimethyl sulfide solution in THF were added at 70° C. under nitrogen atmosphere, and the mixture was subsequently stirred at 70° C. for 2 hours. 579 μl of borane/dimethyl sulfide solution was again added, and the mixture was heated in a heating block at 70° C. for a further 4 hours. In order to decompose the excess borane, 1 ml of MeOH was added dropwise. The reaction mixture was evaporated, and 1 ml of water and 1 ml of conc HCl were added to the oily residue. The mixture was stirred at room temperature for 2 h, rendered alkaline using 2 molar NaOH and extracted with ethyl acetate. The organic phase was dried and purified by column chromatography on silica gel.

Provenance & Evidence