Triethylamine → HCID 90449612, compound

HRID 1411285Notes

Reaction equation

HRID 1411285 reaction equation
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][CH2:4][C:3]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH2:6]2)[CH2:2]1.C(N(CC)CC)C.[CH3:28][Si:29]([CH3:44])([CH3:43])[CH2:30][CH2:31][O:32][C:33](ON1C(=O)CCC1=O)=[O:34]>C(Cl)Cl.O>[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][CH2:4][C:3]2([C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([C:33]([O:32][CH2:31][CH2:30][Si:29]([CH3:44])([CH3:43])[CH3:28])=[O:34])[CH2:6]2)[CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 83670684tert-Butyl spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 90449612HCID 90449612, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-af01a8c433f6489b98ae29b87928676b
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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