Lithium tri-s-butylborohydride → HCID 86640805, compound

To a chilled (−78° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-bromo-pyridin-4-yl)-prop-(E)-ylidene]-amide (6.0 g, 19 mmol) in THF (280 mL) was added a 1 M solution of L-Selectride in THF (37.8 ml, 37.8 mmol) dropwise. After 2.5 hours, the reaction mixture was quenched with saturated aqueous NH4Cl (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×400 mL). The combined organic layers were washed with brine, and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford an oily solid, which after further drying provided 2-methyl-propane-2-sulfinic acid [(R)-1-(2-bromo-pyridin-4-yl)-propyl]-amide as a crystalline solid.

1. customthe reaction mixture was quenched with saturated aqueous NH4Cl (100 mL)
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with EtOAc (2×400 mL)
4. washThe combined organic layers were washed with brine
5. concentrationconcentrated
6. customThe residue was purified by silica gel chromatography
7. washeluting with a gradient of 0-100% EtOAc in hexanes
8. customto afford an oily solid, which
9. customafter further drying

ORD record

ord-d7a06d8149cb4bf2a7133ce5b8240591

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063065B2