Methanesulfonic Acid → HCID 86729319, compound

To a solution of 2-(4-(allyloxy)benzyl)-4-bromo-1-chlorobenzene (2.0 g, 5.92 mmol, prepared as described in Intermediate 1) in dry THF (50 mL), under nitrogen atmosphere, was added nBuLi (4.8 mL, 7.7 mmol, 1.6 M solution in hexanes) at −78° C. The reaction mixture was stirred at the same temperature for 30 min. A solution of (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (3.6 g, 7.7 mol, prepared following the procedure given in US20070049537) in dry THF (40 mL) was added dropwise at the same temperature and stirred for another 3 h. After the completion of the reaction as confirmed by TLC, a solution of methanesulfonic acid (0.76 mL, 11.8 mmol) in methanol (30 mL) was added and the temperature was gradually raised to r.t. and stirred for 16 h. The reaction was quenched by the addition of triethylamine (3.3 mL) and volatiles were evaporated in vacuo. The residue obtained was dissolved in ethylacetate (300 mL) and washed with water (3×20 mL). The organic layers were dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 0.4:9.6 MeOH:DCM) to provide title compound (1.2 g, 45%).

1. additionwas added dropwise at the same temperature
2. stirringstirred for another 3 h
3. customAfter the completion of the reaction
4. stirringstirred for 16 h
5. customThe reaction was quenched by the addition of triethylamine (3.3 mL) and volatiles
6. customwere evaporated in vacuo
7. customThe residue obtained
8. washwashed with water (3×20 mL)
9. dry with materialThe organic layers were dried over anhydrous Na2SO4 and volatiles
10. customwere evaporated in vacuo
11. customThe residue obtained
12. customwas purified by column chromatography (silica gel, 0.4:9.6 MeOH:DCM)

ORD record

ord-306c36b3a0404d3391be9f7c8200e96e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018249B2