Methyl iodide → 2-[(2-Isopropoxy-3-methyl-benzoyl)-methyl-amino]-indan-2-carboxylic acid ethyl ester

To a solution of NaH (sodium hydride, 60% dispersion, 86.0 mg, 2.15 mmol)) in anhydrous THF (20 mL) is added dropwise the solution of 2-(2-isopropoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (6) (410 mg, 1.07 mmol) in THF (5 mL) at 0° C. After stirring for 20 min, methyl iodide (452 μL, 7.26 mmol) is added dropwise and the resulting suspension is warmed up to RT and continued stirring overnight. After being quenched by saturated aqueous solution of ammonium chloride (5 mL), the reaction mixture is diluted in EtOAc (50 mL). The organic layer is separated, washed with water (1×5 mL) and brine (2×5 mL), dried over anhydrous Na2SO4 and concentrated in in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 0%-30% EtOAc in heptane) to give the pure product (118) as a colorless oil (240 mg, 57%).

1. stirringcontinued stirring overnight
2. customAfter being quenched by saturated aqueous solution of ammonium chloride (5 mL)
3. additionthe reaction mixture is diluted in EtOAc (50 mL)
4. customThe organic layer is separated
5. washwashed with water (1×5 mL) and brine (2×5 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated in in vacuo
8. customThe residue is purified by flash column chromatography (115 g silica gel, gradient elution: 0%-30% EtOAc in heptane)

ORD record

ord-809a137d77c24007ba4b79451d0e9c4a

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569535B2