Lithium tri-s-butylborohydride → HCID 86689842, compound

Participants

Reaction Steps

To (R)-ethyl 2-(1-(tert-butylsulfinylimino)ethyl)-5H-pyrrolo[3,2-d]pyrimidine-5-carboxylate (259.0 mg, 0.77 mmol) in anhydrous THF (5 mL) at 0° C. was added dropwise L-selectride (1.0 mol/L) in THF (1.2 mL). The resultant orange reaction mixture was warmed to RT and stirred under N2 for 16 h. The solvent was removed in vacuo and the crude was partitioned between EtOAc and water. The organic layer was washed with sat'd. aq. NaHCO3, water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude was purified by SiO2 chromatography eluted with a mixture of EtOAc containing 1% TEA and MeOH to afford 180.0 mg (87.8%) of (R)—N-(1-(5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethyl)-2-methylpropane-2-sulfinamide as racemic mixture. MS (ESI) m/z: 267 [M+1]+.

Provenance & Evidence