Water → HCID 70984611, compound

HRID 928039Notes

Reaction equation

HRID 928039 reaction equation
I[CH2:2][CH3:3].FC(F)(F)C(O)=O.[NH:11]1[CH2:15][CH2:14][C@@H:13]([CH2:16][NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:2]([N:11]1[CH2:15][CH2:14][C@@H:13]([CH2:16][NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12]1)[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 70983909HCID 70983909, compound2×

Product 1

HCID 70984611HCID 70984611, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Iodoethane (4.1 g) was added to a cooled mixture of benzyl N—((R)-pyrrolidin-3-ylmethyl)carbamate trifluoroacetate salt (Intermediate 171, 7.6 g) and potassium carbonate (12.2 g) in DMF (10 mL) while maintaining the temperature at 0° C. The mixture was then stirred at room temperature for 4 hours. Water was added and the mixture was extracted with ethyl acetate, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give benzyl N—((S)-1-ethylpyrrolidin-3-ylmethyl)carbamate (1.8 g) as a colourless oil, which was used without further characterisation.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-b8bdc21a19ff4878a66fb5c0554fe9ce
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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