Methanol → HCID 131731377, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Step D (18.43 g, 36.0 mmol) in tetrahydrofuran (250 mL) was added borane dimethyl sulfide complex solution (144 mL, 288 mmol, 2.0 M solution in tetrahydrofuran) over 15 min. The reaction was placed in a preheated 70° C. bath and stirred for 75 min. The mixture was cooled to 0° C. and methanol (100 mL) slowly added over 15 min. The ice bath was removed and the mixture stirred for 30 min and the solvent removed in vacuo. The residue was dissolved in ethanol (150 mL) and heated at 70° C. for 4 h, cooled to ambient temperature and the solvent removed in vacuo. The crude solid was purified by column chromatography (silica gel Biotage 40M) eluting with methanol/ethyl acetate (gradient from 0% to 10%) to give the minor (first eluting) diastereomer tert-butyl {(2R,3S,5S)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]piperidin-3-yl}carbamate and the major (second eluting) diastereomer, the title compound as colorless solids. LC/MS 498.2 (M+1).

Provenance & Evidence