Thiazole → HCID 71003680, compound

Thiazole (501 mg, 5.88 mmol) was dissolved in THF (1.2 mL) and isopropylmagnesium chloride lithium chloride complex (1.3 M solution in THF, 5.88 mL, 7.64 mmol) was added dropwise, and the resulting mixture was stirred at room temperature for 1 hr. Cis-methyl 3-acetylcyclopentanecarboxylate (1.2 g, 7.05 mmol) was then added as a solution in THF (2 mL) and the reaction mixture was stirred for 3 hrs at room temperature. The reaction mixture was diluted with saturated NH4Cl and diethyl ether. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (12% to 100% Et2O in Hexanes) to afford cis-methyl 3-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclopentanecarboxylate as a colorless oil; MS ESI calc'd. for C12H18NO3S [M+H]+ 256. found 256.

1. stirringthe reaction mixture was stirred for 3 hrs at room temperature
2. customThe organic layer was separated
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by chromatography on silica gel (12% to 100% Et2O in Hexanes)

ORD record

ord-7999655740f54b38bd54d7c2888c030b

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290490B2