Hydrochloric Acid → 2-(3-Nitro-3-phenyl-propyl)-pyrrolidine

HRID 1097629Notes

Reaction equation

HRID 1097629 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH2:14][CH:15]([N+:22]([O-:24])=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[N+:22]([CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:14][CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)([O-:24])=[O:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 585678972-(3-Nitro-3-phenyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 585679122-(3-Nitro-3-phenyl-propyl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 230 mg (0.688 mmol) 2-(3-nitro-3-phenyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 3.5 ml methanol were added 860 ul (0.3.44 mmol) of a 4M HCl solution in dioxane. The mixture was stirred at room temperature for 17 hours. The solvent was removed in vacuo. The residue was dissolved in water. The mixture was basified with a saturated sodium bicarbonate solution and extracted 6 times with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to provide 96 mg (y: 59.6%) of the title compound as a white solid. MS (m/e): 235.2 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted 6 times with dichloromethane
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-932e9a666a514f118df9a440e2f77987
Source dataset
uspto-grants-2012_03
Patent number
US08143273B2

Reaction notes

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