Lithium tri-s-butylborohydride → HCID 86640807, compound

Participants

Reaction Steps

To a chilled (−78° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-bromopyridin-4-yl)-eth-(E)-ylidene]-amide (9.3 g, 31 mmol) in THF (280 mL) is added a 1 M solution of L-Selectride in THF (61.3 mL, 61.3 mmol) dropwise. After 2.5 hours, the chilled mixture is quenched with saturated aqueous NH4Cl (100 mL). The layers are separated and the aqueous layer is extracted with EtOAc (2×400 mL). The combined organic layers are washed with brine, and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 50-90% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-bromopyridin-4-yl)-ethyl]-amide as an oil which contained 5% of the opposite diastereomer.

Provenance & Evidence