Dimethylformamide → HCID 67421029, compound

HRID 1037982Notes

Reaction equation

HRID 1037982 reaction equation
[CH:1]([N:4]([CH:7]([CH3:9])C)CC)([CH3:3])C.[C:10](=[O:13])([O-:12])[O-].[Cs+].[Cs+].[C:16]([O:20][C:21](=[O:24])[CH2:22]Br)([CH3:19])([CH3:18])[CH3:17].[CH3:25]N(C)C=O>[Cl-].[Na+].O>[CH3:25][O:12][C:10]([CH:9]1[CH2:3][CH2:1][N:4]([CH2:22][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:24])[CH2:7]1)=[O:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 67421029HCID 67421029, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

R-pyrrolidine-3-carboxylic acid methyl ester (1.5 gm, 9.1 mmol) was dissolved in N,N-dimethylformamide (45 ml). Diisopropylethylamine (5.7 ml, 31 ml) was added followed by cesium carbonate (4.35 gm, 13.3 mmol). Tert. butylbromoacetate (1.5 ml, 10 mmol) was added dropwise and the reaction mixture stirred for 1 hr. Brine was added to the reaction mixture which was then extracted with ethylacetate three times. The ethylacetate extracts were dried over magnesium sulfate, filtered and evaporated to obtain crude title product. The crude product was chromatographed to obtain 2.15 gm, 97% of title product.

Workup

  1. extractionwas then extracted with ethylacetate three times
  2. dry with materialThe ethylacetate extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto obtain crude title product
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-fd2bf156e1fa410abcc22fca8fd192f8
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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