Water → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

HRID 1411311Notes

Reaction equation

HRID 1411311 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].Br[CH2:17][C:18]1[CH:19]=[C:20]2[C:26]3([CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]3)[CH2:25][N:24]([C:38]([O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])=[O:39])[C:21]2=[CH:22][CH:23]=1.O>C(O)C>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:17][C:18]1[CH:19]=[C:20]2[C:26]3([CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[CH2:27]3)[CH2:25][N:24]([C:38]([O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])=[O:39])[C:21]2=[CH:22][CH:23]=1)[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 904495541-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(bromomethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Product 1

HCID 904497891-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl malonate (183 mg, 1.14 mmol) was dissolved in ethanol (2 mL). Thereafter, sodium ethoxide (78.0 mg, 1.15 mmol) and an ethanol (2 mL) solution of 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(bromomethyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (390 mg, 0.76 mmol) 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 1.5 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. 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=3:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (300 mg, 67%) in the form of a colorless amorphous product.

Workup

  1. temperatureunder cooling on ice
  2. extractionthe mixed solution was then extracted with ethyl acetate
  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=3:1)

Sources & evidence

ORD record
ord-dc1bdd164b2a41d5a6fccc64fd84386e
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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