Lithium tri-s-butylborohydride → HCID 86689831, compound

Participants

Reaction Steps

To a solution of (R)-tert-butyl 5-(1-(tert-butylsulfinylimino)ethyl)-1H-pyrrolo[3,2-b]-pyridine-1-carboxylate (1.18 g, 3.25 mmol) in anhydrous THF (21.1 mL) at 0° C. was added dropwise L-selectride (1.0 mol/L) in THF (4.9 mL). The resultant orange reaction mixture was warmed to RT and stirred under N2 for 3 h. The solvent was removed in vacuo, and the crude product was purified by SiO2 chromatography eluting with MeOH/EtOAc+1% TEA to afford 700 mg (81.3%) of (R)—N—((S)-1-(1H-pyrrolo[3,2-b]-pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide as a foam (95% ee). The enantiomers were separated via chiral SFC chromatography to give 597.0 mg (100% ee) of (R)—N—((S)-1-(1H-pyrrolo[3,2-b]-pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide: 1H NMR (400 MHz, MeOD) δ 7.79 (d, J=8.5 Hz, 1H), 7.55 (d, J=3.3 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 6.58 (d, J=3.1 Hz, 1H), 4.73-4.66 (m, 1H), 1.63 (d, J=6.9 Hz, 3H), 1.19 (s, 9H); MS (ESI) m/z: 266.3 [M+1]+.

Provenance & Evidence