(Dimethyl sulfide)trihydroboron → HCID 70011993, compound

Participants

Reaction Steps

Borane-methyl sulfide complex (1.68 mL, 2.0 M solution in THF) was added drop wise to stirred solution of the product of Step 1 (224 mg) in dry THF (5 mL) under nitrogen. After 16 h at room temperature, the solution was cooled, and excess borane was quenched with methanol. The solvent was evaporated to dryness, and the residue was dissolved in THF (5 mL). 2-(Dimethylamino)ethanol (0.67 mL) was added, and the reaction mixture was heated under reflux for 3 h, cooled, and evaporated to dryness. The residue was purified by preparative TLC (CH2Cl2—MeOH, 90:10) to give the title compound (50 mg). NMR (CD3OD): 0.54-0.59 (m, 2H, cyclopropyl),0.75-0.77 (m, 2H, cyclopropyl),1.85, 2.02, 2.32, 2.61 (4 m, 8H, piperidinyl),2.64-2.69 (m, 1H, CH),3.26-3.29 (d, 2H, CH2),6.20 (s, 1H, H-4),7.08-7.11 (m, 2H, H-2 & H-6 of 4-F-phenyl),7.24-7.26 (m, 2H, H-2 & H-6 of pyridinyl),7.33-7.37 (m, 2H, H-3 & H-5 of 4-F-phenyl),8.24-8.26 (m, 2H, H-3 & H-5 of pyridinyl)

Provenance & Evidence