Lithium tri-s-butylborohydride → HCID 86689870, compound

Participants

Reaction Steps

To (R)-ethyl 5-(1-((tert-butylsulfinyl)imino)ethyl)-3-chloro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (2.06 g, 5.569 mmol) in anhydrous THF (36.2 mL) at 0° C. was added dropwise L-selectride (1.0 mol/L) in THF (8.4 mL). The resultant orange reaction mixture was then warmed to RT and stirred at this temperature under N2 for 16 h. Volatile solvent was removed under reduced pressure, and the crude residue was diluted with EtOAc. The EtOAc layer was washed with sat'd. aq. NaHCO3, water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with MeOH/EtOAc+1% TEA. Trituration with DCM afforded 1.08 g (65.03%) of (R)—N—((S)-1-(3-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-2-methylpropane-2-sulfinamide as pale yellow solid (100% ee). 1H NMR (400 MHz, DMSO) δ 11.52 (s, 1H), 7.80 (d, J=8.5 Hz, 1H), 7.77 (s, 1H), 7.29 (d, J=8.5 Hz, 1H), 5.43 (d, J=5.4 Hz, 1H), 4.62-4.51 (m, 1H), 1.53 (d, J=6.8 Hz, 3H), 1.11 (s, 9H); MS (ESI) m/z: 300.0 [M+1]+.

Provenance & Evidence