Triethylamine → HCID 90449612, compound

t-Butyl spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (10.0 g, 36.4 mmol) was dissolved in methylene chloride (73 mL). Thereafter, triethylamine (15.2 mL, 109 mmol) and N-[2-(trimethylsilyl)ethoxycarbonyloxy]succinimide (14.2 g, 54.8 mmol) were added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 22 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (16.1 g, quant.) in the form of a light yellow oily product.

1. temperatureunder cooling on ice
2. extractionwas then extracted with chloroform
3. washThe organic layer was washed with brine
4. dry with materialwas then dried over anhydrous sodium sulfate
5. concentrationfollowed by concentration in vacuo
6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

ORD record

ord-af01a8c433f6489b98ae29b87928676b

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921576B2