2,6-Lutidine → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-formylspiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

HRID 1411308Notes

Reaction equation

HRID 1411308 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1)=C.I([O-])(=O)(=O)=[O:33].[Na+].N1C(C)=CC=CC=1C.S([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O.O>[CH:1]([C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1)=[O:33]

Participants

8

Reactant 4

HCID 79372,6-LutidineHCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 90449481HCID 90449481, compound

Product 1

HCID 904497561-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-formylspiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylateYield 82%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-vinylspiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (674 mg, 1.52 mmol) was dissolved in dioxane (15 mL). Thereafter, sodium periodate (1.30 g, 6.08 mmol), water (5 mL), 2,6-lutidine (0.35 mL, 3.01 mmol), and osmium tetroxide (1% t-butanol aqueous solution, 1 mL) were added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 3 hours. Thereafter, an aqueous solution of sodium sulfite was added to the reaction solution, and the mixture 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 5-formylspiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (553 mg, 82%) in the form of a light yellow solid.

Workup

  1. temperatureunder cooling on ice
  2. extractionthe mixture was 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-424e45b2085e450fb6fd2c1dc148be2a
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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