Lithium Hexamethyldisilazide → HCID 118590475, compound

(S,Z)—N-(4-chloro-1-(5-fluoro-2-(((R)-tetrahydrofuran-3-yl)oxy)phenyl)butylidene)-2-methylpropane-2-sulfinamide (7.6 g, 19.5 mmol) in THF (100 mL) was cooled to −78° C. and to which was added cold (−78° C.) Lithium triethylborohydride (1M in THF) (21.48 ml, 21.5 mmol) drop wise and stirring was continued at −78° C. for 3 h. LiHMDS (1M in THF) (19.53 ml, 19.5 mmol) was then added and stirring was continued at −78° C. to 0° C. for 2 h. The resultant reaction mixture was quenched with saturated NH4Cl solution, diluted with ethyl acetate. The ethyl acetate layer separated was washed with water followed by brine solution, dried over anhydrous sodium sulphate and concentrated under reduce pressure to afford the crude residue. The residue thus obtained was purified by column chromatography twice (using initially with 60-120 silica gel and 15% EtOAc in Hexane as elute and again with 230-400 silica gel and 12-14% EtOAc in Hexane as elute) to afford 4.1 g of the title compound as crude, which was used as such for the next step.

1. stirringstirring
2. waitwas continued at −78° C. to 0° C. for 2 h
3. customThe resultant reaction mixture
4. customwas quenched with saturated NH4Cl solution
5. additiondiluted with ethyl acetate
6. customThe ethyl acetate layer separated
7. washwas washed with water
8. dry with materialdried over anhydrous sodium sulphate
9. concentrationconcentrated
10. customto afford the crude residue
11. customThe residue thus obtained
12. customwas purified by column chromatography twice (
13. washas elute and again with 230-400 silica gel and 12-14% EtOAc in Hexane
14. washas elute)

ORD record

ord-c9a1a13d46e643f5a9af8a67e4e7abea

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394305B2