Hydrochloric Acid → HCID 68626334, compound

HRID 1801513Notes

Reaction equation

HRID 1801513 reaction equation
C(OC([NH:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=O)(C)(C)C.[H-].[Na+].[CH3:16][O:17][CH2:18][CH2:19]Br.[ClH:21].O1CCOCC1>CN(C=O)C.CCOC(C)=O.O>[ClH:21].[ClH:21].[CH3:16][O:17][CH2:18][CH2:19][N:11]1[CH2:12][CH2:13][CH:9]([NH2:8])[CH2:10]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 809722-Bromoethyl methyl etherHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 68626334HCID 68626334, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(t-Butoxycarbonylamino)pyrrolidine (1 g, 1 eq) is dissolved in DMF (15 mL) and NaH 60% in oil (258 mg, 1.2 eq) is added followed by 2-bromoethyl methyl ether (656 μL, 1.3 eq). Water (150 mL) and EtOAc (150 mL) are added and the two layers are separated. The aqueous layer is extracted with EtOAc (2×150 mL). The combined organic layers are washed with brine, dried over MgSO4 filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (100% EtOAc). The isolated compound (300 mg, 23%) is dissolved in dioxane (2 mL) and HCl 4 M solution in dioxane (5 mL, 20 eq) is added. The solution is stirred for 1 h and the reaction mixture is then concentrated and co-evaporated with toluene to afford 1-(2-methoxy-ethyl)-pyrrolidin-3-ylamine 2HCl (266 mg, 100%).

Workup

  1. customthe two layers are separated
  2. extractionThe aqueous layer is extracted with EtOAc (2×150 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography (100% EtOAc)
  8. dissolutionThe isolated compound (300 mg, 23%) is dissolved in dioxane (2 mL)
  9. concentrationthe reaction mixture is then concentrated and co-evaporated with toluene

Sources & evidence

ORD record
ord-e4cf464fb5274c1e91194b2e89d60d5f
Source dataset
uspto-grants-2013_01
Patent number
US08349839B2

Reaction notes

Loading…