Methanol → HCID 90449400, compound

HRID 1411247Notes

Reaction equation

HRID 1411247 reaction equation
CO.O.C(=O)([O-])[O-].[K+].[K+].[Cl:10][C:11]1[CH:12]=[C:13]2[C:19]3([CH2:23][CH2:22][N:21]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]3)[CH2:18][N:17](C(=O)C(F)(F)F)[C:14]2=[CH:15][CH:16]=1>C(OCC)(=O)C>[Cl:10][C:11]1[CH:12]=[C:13]2[C:19]3([CH2:23][CH2:22][N:21]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]3)[CH2:18][NH:17][C:14]2=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 90449753HCID 90449753, compound

Product 1

HCID 90449400HCID 90449400, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methanol (10.7 mL), water (3.6 mL), and potassium carbonate (0.4 g, 2.86 mmol) were added to t-butyl 2-(5-chloro-1-(2,2,2-trifluoroacetyl)spiro[indoline-3,3′-pyrrolidin]-1′-yl)acetate (0.6 g, 1.43 mmol), and the obtained mixture was then stirred at room temperature for 1.5 hours. Thereafter, the reaction solution was diluted with ethyl acetate, and was then washed with water and brine. The organic layer was concentrated in vacuo to obtain t-butyl 2-(5-chlorospiro[indoline-3,3′-pyrrolidin]-1′-yl)acetate (0.47 g, >100%) in the form of a light brown oily product.

Workup

  1. washwas then washed with water and brine
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-9c256b324ca84dc29662d020dde4efea
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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