Sodium Bicarbonate → HCID 86642499, compound

HRID 1631975Notes

Reaction equation

HRID 1631975 reaction equation
Cl.[CH2:2]([N:9]([CH2:13][CH2:14]Cl)[CH2:10][CH2:11]Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:16]([N:23]1[CH2:27][CH2:26][C@@H:25]([NH2:28])[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:2]([N:9]1[CH2:13][CH2:14][N:28]([C@@H:25]2[CH2:26][CH2:27][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:24]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochloride

Product 1

HCID 86642499HCID 86642499, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.99 g (21.5 mmol) of benzylbis(2-chloroethyl)amine hydrochloride (XX) were dissolved in ethanol (120 ml) and, while stirring, 4.00 g (21.5 mmol) of (R)-(+)-N-Boc-3-aminopyrrolidine and 7.22 g (85.9 mmol) of sodium bicarbonate were added. The resulting reaction solution was heated under reflux for 4 h. The cooled reaction mixture was concentrated in vacuo, 100 ml of water were added, and the aqueous phase was extracted with ethyl acetate (4×60 ml). The combined organic phases were washed with saturated aqueous NaHCO3 solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 0-5% methanol in dichloromethane). Yield: 4.48 g (60%) of yellow solid

Workup

  1. customThe resulting reaction solution
  2. temperaturewas heated
  3. temperatureunder reflux for 4 h
  4. customThe cooled reaction mixture
  5. concentrationwas concentrated in vacuo, 100 ml of water
  6. additionwere added
  7. extractionthe aqueous phase was extracted with ethyl acetate (4×60 ml)
  8. washThe combined organic phases were washed with saturated aqueous NaHCO3 solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography on silica gel (mobile phase gradient 0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-60cc0aecdf9545cfafd099a62c7987c5
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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