Potassium Carbonate → HCID 90449363, compound

HRID 1411270Notes

Reaction equation

HRID 1411270 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([SH:17])[CH:15]=3)[N:10]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br-].[CH2:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>CN(C)C=O.O>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:17][CH:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[CH:15]=3)[N:10]([C:18](=[O:23])[C:19]([F:21])([F:22])[F:20])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22031976HCID 22031976, compoundHCID 90449477HCID 90449477, compound

Product 1

HCID 90449363HCID 90449363, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(1′-Acetyl-5-mercaptospiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (26 mg, 0.076 mmol) was dissolved in dimethylformamide (1 mL). Thereafter, potassium carbonate (32 mg, 0.23 mmol) and cyclopentane bromide (23 mg, 0.15 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 1.5 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous magnesium sulfate, followed by concentration in vacuo. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1) to obtain 1-(1′-acetyl-5-(cyclopentylthio)spiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (13 mg, 42%) in the form of a colorless oily product.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-b2977832c0c44f108d3745049a9b4d7b
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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